Prosecution Insights
Last updated: October 04, 2026
Application No. 16/760,661

1,3-PROPYLENE ETHER DERIVED COMPOUNDS FOR PERSONAL CARE

Non-Final OA §103
Filed
Apr 30, 2020
Priority
Nov 01, 2017 — provisional 62/579,991 +1 more
Examiner
PAGANO, ALEXANDER R
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Croda International plc
OA Round
6 (Non-Final)
79%
Grant Probability
Favorable
6-7
OA Rounds
0m
Est. Remaining
90%
With Interview

Examiner Intelligence

Grants 79% — above average
79%
Career Allowance Rate
848 granted / 1077 resolved
+18.7% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Fast prosecutor
2y 1m
Avg Prosecution
46 currently pending
Career history
1131
Total Applications
across all art units

Statute-Specific Performance

§101
3.9%
-36.1% vs TC avg
§103
23.1%
-16.9% vs TC avg
§102
31.3%
-8.7% vs TC avg
§112
26.3%
-13.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1077 resolved cases

Office Action

§103
DETAILED ACTION The Examiner inherited this application from another Examiner. 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 . This Office Action is in response to Applicant’s Arguments filed on 01/21/2025, wherein no claims have been amended, canceled or added by this Response. Status of Claims Claims 1, 3-6, 17, 18 and 22-29 are rejected. Claims 7-9, 16 and 19-21 are withdrawn from further consideration. Claims 2 and 10-15 are canceled. Claims 1, 3-9 and 16-29 are pending. Response to Arguments Applicant's arguments filed January 21, 2025 have been fully considered but they are not persuasive. Claim Rejections - 35 USC § 103 On page 5, second paragraph under “Rejection under 35 U.S.C. 103”, Applicant argues that “none of Carmichael, Kulkarni, JP2007519777, Gokel, Nuwala and Boardman teaches or suggests a superior effect associated with the unbranched 3-carbon unit (OCH2CH2CH2) ("PPD") compared to the following branched 3-carbon unit ("PPG") described in Carmichael: PNG media_image1.png 200 400 media_image1.png Greyscale ” As pointed out in the final rejection dated February 2, 2024, and the Non-Final rejection for the RCE dated October 22, 2024, Carmichael et al. disclose an emollient oil for use in an inverse emulsion comprising esters of long chain fatty acids and alkoxylated fatty aliphatic alcohols of the formula (I) PNG media_image2.png 353 852 media_image2.png Greyscale (column 3, lines 11-26 and claim 1). The long chain fatty acids in the esters of the alkoxylated fatty aliphatic alcohols are desirably C8 to C24, especially C10 to C18 fatty acids. The fatty acids can be straight chain or branched, and saturated or unsaturated, and suitable fatty acids include lauric, myristic, palmitic, stearic, iso-steric, oleic and linoleic acids. The fatty alcohols used in these esters are desirably C8 to C20, especially C10 to C18. The fatty alcohols may be straight chain or branched, and may be saturated or unsaturated. Suitable examples of the fatty alcohols include 2-ethylhexyl, lauryl, myristyl, palmityl, palmitoleyl, stearyl, iso-stearyl, oleyl and linoleyl (column 4, lines 23-34). Carmichael et al. disclose that AO1 in their formula (I) is selected from propyleneoxy group (column 3, lines 21-23). Nowhere in Carmichael et al. is the propyleneoxy group limited to PNG media_image3.png 112 154 media_image3.png Greyscale . Carmichael teaches “each group AO1 is independently an alkyleneoxy group, particularly an ethyleneoxy or propyleneoxy group;” (col 3, line 20) which includes PPD. “A person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely the product not of innovation but of ordinary skill and common sense.” KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385, 1395-97 (2007). Kulkarni et al. disclose sulfate-free personal care compositions, which include structured surfactants (paragraph 0002). Kulkarni et al. disclose that the term “alkyleneoxy” means a bivalent straight or branched acyclic ether or polyether radical such as, for example, ethyleneoxy, poly(ethyleneoxy), propyleneoxy, poly(propyleneoxy) and poly(ethoxylenepropyleneoxy) (paragraph 0036). JP 2007519777 A disclose latex paint compositions and coatings (Technical-Field on page 2). JP 2007519777 A disclose that the propyleneoxy moiety can be branched or straight chain (see the last paragraph on page 5). Gokel discloses crown ethers (page 326). Gokel discloses that the propyleneoxy units have the formula (OCH2CH2CH2) (the last paragraph on page 326). Nulwala et al. disclose an ionic liquid solvent for use in a variety of applications (Abstract). Nulwala et al. disclose that AO represents alkyleneoxy moieties, such as propyleneoxy units having the formula (OCH2CH2CH2) (paragraph 4 on page 11). Boardman et al. disclose the use of an encapsulated phase change material to improve the beneficial effect of an additional encapsulated material, which is volatile beneficial agent (Tissue treatment Technical Field on page 2). Boardman et al. disclose that polyoxyalkyleneoxy facilitates the water solubility of the polymer. Preferably the polyoxyalkyleneoxy [-O(CH2)w-] sO is selected from polyoxy-1,2-propyleneoxy [-OCH2 (CH)Me)-] sO-; polyoxy-1,3-propyleneoxy [-OCH2CH2CH2)-] sO-; and polyoxy-1,2-ethyleneoxy [-OCH2CH2)-]sO- (paragraph 7 on page 6). Thus, one having ordinary skill in the art before the effective filing date of the claimed invention would have reasonably expected the term “propyleneoxy” to include unbranched and branched propyleneoxy units for the AO1 moiety in the formula (I) ester of Carmichael et al., since Carmichael et al. disclose that AO1 in their formula (I) can be selected from the propyleneoxy group and Kulkarni et al., JP 2007519777 A, Gokel, Nulwala et al. and Boardman et al. have shown that it is well known that propyleneoxy moiety can be branched or straight chain and in particular that propyleneoxy units are known to have the formula (OCH2CH2CH2). “A person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely the product not of innovation but of ordinary skill and common sense.” KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385, 1395-97 (2007). Further, A reference need not disclose what is well known in the art. In re MYERS, 161 USPQ 668 (CCPA 1969). Both of the declaration filed under 37 C.F.R. 1.132 on July 9, 2024, and the 2025 publication directed to hair treatment comparisons filed with this Argument on January 21, 2025, have been fully considered but they are not persuasive for the following reasons. On the last paragraph of page 5, Applicant cites the prior submitted 1.132 Saporito declaration for demonstrating unexpected advantages associated with exemplary personal care products containing a PPD component compared to personal care products containing a PPG component. Applicants further discusses the advantages shown in the declaration. However, the comparison results do not overcome the prima facie case of obviousness because: An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979). However, Cromollient TM CD3-A (Comp. Example 1) and Crodamol TM STS (Comp. Example 2) are not representative of the esters of long chain fatty acids and alkoxylated fatty aliphatic alcohols having formula (I) disclosed by Carmichael et al. (the closest prior art). In particular, esters of long chain fatty acids and alkoxylated fatty aliphatic alcohols as disclosed in column 4, lines 27-34. Second, the showing in the declaration is not commensurate in scope with the claims. "Objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). In addition, the pair of compounds used for comparison differ in more than one structural point, it is difficult to conclude that the advantages come from the unbranched 3-carbon unit. For example, as acknowledged by the Applicant, “Inventive Example 1 and Comparative Example 1 differ in both their alcohol and acid components, another difference is that the inventive example contains 5 PPD groups while the comparative example contains 3 PPG groups. One or more of these differences could be contributing to the superior performance observed with Inventive Example 1.” The submitted 2025 publication also does not overcome the prima facie case of obviousness for the same reasons discussed above. For the above reasons, the rejection of claims 1, 3-6, 17, 18 and 22-29 under 35 U.S.C. 103 as being unpatentable over Carmichael et al. (US 9,044,622 B2) in view of Kulkarni et al. (US 2015/0044157 A1), JP 2007519777 A (Machine generated English translation pages 1-20), Gokel (“Crown Ethers, Encyclopedia of Supramolecular Chemistry, p. 326, 2004), Nulwala et al. (WO 2015/157441 A1) and Boardman et al. (ES 2587553 T3, machine generated English translation pages 1-30) is maintained. 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 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. This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. Claims 1, 3-6, 17, 18 and 22-29 are rejected under 35 U.S.C. 103 as being unpatentable over Carmichael et al. (US 9,044,622 B2) in view of Kulkarni et al. (US 2015/0044157 A1), JP 2007519777 A (Machine generated English translation pages 1-20), Gokel (“Crown Ethers, Encyclopedia of Supramolecular Chemistry, p. 326, 2004), Nulwala et al. (WO 2015/157441 A1) and Boardman et al. (ES 2587553 T3, machine generated English translation pages 1-30) for the reason given in the previous office action dated October 22, 2024, and the reason discussed above. The instant claims are directed to a compound of the formula (1) PNG media_image4.png 172 616 media_image4.png Greyscale , a personal care product comprising the compound of formula (1) and the personal care product wherein the product comprises the compound as a rheology modifier. Carmichael et al. disclose an emollient oil for use in an inverse emulsion comprising esters of long chain fatty acids and alkoxylated fatty aliphatic alcohols of the formula (I) PNG media_image5.png 254 612 media_image5.png Greyscale (column 3, lines 11-26 and claim 1). The long chain fatty acids in the esters of the alkoxylated fatty aliphatic alcohols are desirably C8 to C24, especially C10 to C18 fatty acids. The fatty acids can be straight chain or branched, and saturated or unsaturated, and suitable fatty acids include lauric, myristic, palmitic, stearic, iso-steric, oleic and linoleic acids. The fatty alcohols used in these esters are desirably C8 to C20, especially C10 to C18. The fatty alcohols may be straight chain or branched, and may be saturated or unsaturated. Suitable examples of the fatty alcohols include 2-ethylhexyl, lauryl, myristyl, palmityl, palmitoleyl, stearyl, iso-stearyl, oleyl and linoleyl (column 4, lines 23-34). The alkoxylation will typically be formed of ethyleneoxy or propyleneoxy groups or combinations thereof (column 4, lines 35-38). Carmichael et al. disclose a personal care product comprising an inverse emulsion having the esters of long chain fatty acids and alkoxylated fatty aliphatic alcohols of the formula (I) (claim 3). Carmichael et al. disclose that the primary application of the inverse emulsions is to provide the water soluble polymers in personal care products (column 9, line 66 to column 10, line 6). The main effect of including the polymers is to thicken the end products with a gain in product attributes from the enhanced emollient performance and/or benefits to product rheology (column 10, lines 1-6). In the formula (I) compound of Carmichael et al. R1 corresponds to the claimed R1, AO1 corresponds to the claimed OCH2CH2CH2, n1 corresponds to the claimed n, and R2 corresponds to the claimed R. Carmichael et al. disclose the claimed invention as described above, but differs from the instant claims in that Carmichael et al. do not expressly require that AO1 is the claimed OCH2CH2CH2. However, Carmichael et al. disclose that AO1 in their formula (I) is selected from an propyleneoxy group (column 3, lines 21-23). Kulkarni et al. disclose sulfate-free personal care compositions, which include structured surfactants (paragraph 0002). Kulkarni et al. disclose that the term “alkyleneoxy” means a bivalent straight or branched acyclic ether or polyether radical such as, for example, ethyleneoxy, poly(ethyleneoxy), propyleneoxy, poly(propyleneoxy) and poly(ethoxylenepropyleneoxy) (paragraph 0036). JP 2007519777 A disclose latex paint compositions and coatings (Technical-Field on page 2). JP 2007519777 A disclose that the propyleneoxy moiety can be branched or straight chain (see the last paragraph on page 5). Gokel discloses crown ethers (page 326). Gokel discloses that the propyleneoxy units have the formula (OCH2CH2CH2) (the last paragraph on page 326). Nulwala et al. disclose an ionic liquid solvent for use in a variety of applications (Abstract). Nulwala et al. disclose that AO represents alkyleneoxy moieties, such as propyleneoxy units having the formula (OCH2CH2CH2) (paragraph 4 on page 11). Boardman et al. disclose the use of an encapsulated phase change material to improve the beneficial effect of an additional encapsulated material, which is volatile a beneficial agent (Tissue treatment Technical Field on page 2). Boardman et al. disclose that polyoxyalkyleneoxy facilitates the water solubility of the polymer. Preferably the polyoxyalkyleneoxy [-O(CH2)w-] sO is selected from polyoxy-1,2-propyleneoxy [-OCH2 (CH)Me)-] sO-; polyoxy-1,3-propyleneoxy [-OCH2CH2CH2)-] sO-; and polyoxy-1,2-ethyleneoxy [-OCH2CH2)-]sO- (paragraph 7 on page 6). One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to select a propyleneoxy having the formula (OCH2CH2CH2) as the AO1 moiety in the formula (I) ester of Carmichael et al., since Carmichael et al. disclose that AO1 in their formula (I) can be selected from the propyleneoxy group and Kulkarni et al., JP 2007519777 A, Gokel, Nulwala et al. and Boardman et al. have shown that it is well known that propyleneoxy moiety can be branched or straight chain and in particular that propyleneoxy units are known to have the formula (OCH2CH2CH2). “A person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely the product not of innovation but of ordinary skill and common sense.” KSR International Co. v. Teleflex Inc., 550 U.S.___, 82 USPQ2d 1385, 1395-97 (2007). Further, A reference need not disclose what is well known in the art. In re MYERS, 161 USPQ 668 (CCPA 1969). Carmichael et al. disclose the claimed invention as described above, but differs from claim 6 in that Carmichael et al. do not expressly disclose the compound caprylate/caprate-(OCH2CH2CH2)5-O-isostearyl. However, Carmichael et al. suggest the claimed compound, since in the formula (I) compound of Carmichael et al. R1, which corresponds to the claimed R1 can be a C7 or C23 hydrocarbyl group; AO1, which corresponds to the claimed CH2CH2CH2-O can be a propyleneoxy group; n1, which corresponds to the claimed n can be from 1 to 15, particularly 1-5; and R2, which corresponds to the claimed R can be C8 to C20 aliphatic group, in particular an alkyl, alkenyl, or alkynyl group (column 3, lines 15-26). In addition, the compounds of Carmichael et al. have the same or similar utility as the instant compounds. A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) (discussed in more detail below) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990). Conclusion No claims are allowed. 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 extension fee 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 date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to XIAOBIN (Amy) DING whose telephone number is (703)756-1409. The examiner can normally be reached Monday-Friday 10a-6p. 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, Robert Havlin can be reached on 571-272-9066. 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. /XD/ Examiner, Art Unit 1692 /ROBERT H HAVLIN/Supervisory Patent Examiner, Art Unit 1692
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Prosecution Timeline

Show 16 earlier events
Apr 09, 2025
Notice of Allowance
Apr 14, 2025
Response after Non-Final Action
Jun 17, 2025
Response after Non-Final Action
Aug 13, 2025
Response after Non-Final Action
Aug 14, 2025
Response after Non-Final Action
Aug 15, 2025
Response after Non-Final Action
Aug 15, 2025
Response after Non-Final Action
May 28, 2026
Response after Non-Final Action

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Prosecution Projections

6-7
Expected OA Rounds
79%
Grant Probability
90%
With Interview (+11.3%)
2y 1m (~0m remaining)
Median Time to Grant
High
PTA Risk
Based on 1077 resolved cases by this examiner. Grant probability derived from career allowance rate.

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