DETAILED ACTION
Election/Restrictions
Applicant’s election without traverse of Group IV, claims 14-16 and new claims 21-37 in the reply filed on 22 December 2025 is acknowledged.
The non-elected claims 1-15 and 17-20 have been canceled.
Non-Compliant Amendment
Applicant’s amendment dated 22 December 2025 is noncompliant, because the claims include two different claims numbered “22”. Since both claims are of similar scope and are currently under rejection, the claims will be examined below, indicating a first and second instance of claim 22 where appropriate. Please amend to correct the claim numbering.
Claim Objections
Claim 37 is objected to because of the following informalities: the phrase “the coating compositions comprises” should be “the coating composition comprises”. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 25-28 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 14 requires a monomer of Formula (III) containing a Z group reactive with epichlorohydrin. Claims 25 and 26 state that the monomer of Formula III is one of Formula IV or V, in which the Z group is replaced with a Z2 group that is a residue of Z after reaction with epichlorohydrin. As such, claims 25-28 fail to include all of the limitations of claim 14. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 14, 15, 21, 22 (first and second instance), 29-33 and 36 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Rao and Samui, “Phase Behavior and Photo-Responsive Studies of Photoactive Liquid Crystalline Hyperbranched Polyethers Containing Benzylidene Moiety,” J. Polym. Sci. Part A: Polym. Chem 47, 2774-2786 (2009) (“Rao A”).
AS to claim 14, 21, and 22 (first and second instances) and 29, Rao A teaches a polyether polymer formed using a benzylidene monomer (abstract). As one example, Rao A teaches a monomeric diol 1,3-bis(3-methoxy-4-hydroxy benzylidene)-cyclohexanone (Diol-C6,2) (p. 2777). This diol meets formula (III) where R2 and R3 are each organic groups that are fused in a ring, Y is hydrogen, n is 0, A is aromatic ring, Z is hydroxy (a group reactive with epichlorohydrin), R1 is a methoxy (organic) group, and t is 1. The aforementioned compound meets Formula IIIA of claim 21 where each R5 is hydrogen, Formula IIIB of claim 22 (first instance) where three R1 groups on each phenyl group are hydrogen and one is methoxy, and is the same as Formula IIIC of claim 22 (second instance).
Rao A teaches reacting this diphenolic compound with triphenylolmethane triglycidyl ether (p. 2777) to form a hyperbranched polymer.
As to claim 15, Rao A teaches reacting equimolar amounts of the diol and triglycidyl ether (p. 2777). Given the relative molecular weights, it is calculated that the resulting polymer is approximately 45 wt % of the monomer of formula (III).
As to claim 30, Rao A teaches the polymers having a Tg of the recited range (Table 1, p. 2780).
As to claim 31, Rao A teaches the polymers having Mn in the recited range (Table 1, p. 2780).
As to claim 32, Rao A teaches the polymer having the recited backbone segments (see Scheme 1, p. 2778, showing recited linkages arising from reaction of glycidyl and phenol groups).
As to claim 33, Rao A teaches polydispersity of the polymers in the recited range (Table 1, p. 2780).
As to claim 36, the resulting polymer lacks bisphenol A, bisphenol F, or bisphenol S units (see Scheme 1).
Claim(s) 14, 15, 21, 22 (first and second instance), 25-27, 29-33, and 36 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Rao and Samui, “Molecular Engineering of Photoactive Liquid Crystalline Polyester Epoxies Containing Benzylidene Moiety,” J. Polym. Sci. Part A: Polym. Chem. 16, 7637-7655 (2008) (“Rao B”).
Rao B was included with applicant’s IDS dated 16 August 2024.
As to claims 14, 21, and 22, Rao B teaches a polyester polymer formed from an epoxy resin and polyacids. Rao B, as one example, teaches a diepoxide formed from 2,6-bis-(3-methoxy-4-hydroxybenzylidene)cyclohexanone, the compound meeting Formula (III) where R2 and R3 are organic groups that are fused in a ring, t is 4, three R1 are hydrogen and one is a methoxy group, Y is hydrogen, n is 0, A is an aromatic group, Z is a hydroxyl group reactive with epichlorohydrin. This compound meets Formula IIIA of claim 21 where each R5 is hydrogen, and meets Formula IIIB of claim 22 (first instance) and Formula IIIC of claim 22 (second instance).
Rao B states forming the polymer from a diepoxide derivative of the aforementioned compound, not the compound itself. However, this limitation is construed as a product by process limitation, for which patentability is determined by the end product. Rao B teaches the diol is reacted with epicholorhydrin to obtain the corresponding epoxy resin (p. 7642), and the resulting diepoxide is reacted with diacids and/or triacids to form the polyester (p. 7643, 7646). This is deemed to be have the same structure as a polyester formed by reacting the diol of the recited formula with glycidyl esters of the diacids and triacids.
As to claim 15, the polymer contains more than 5 wt % of units equivalent to those derived from the compound of Formula III.
As to claims 25-27, Rao B teaches a polyester polymer formed from an epoxy resin and polyacids. Rao B, as one example, teaches a diepoxide 2,6-bis-(3,5-dimethoxy-4-epoxypropoxybenzylidene)cyclohexanone (p. 764), which meets Formula (IV) where R2 and R3 are each organic groups that are fused in a ring, n is 0, A is an aromateic ring, t is 4, three of R1 are hydrogen, one of R1 is methoxy, Z2 is -O-. This meets Formula (IVA) of claim 26 where each R5 is H, and Formula IVB of claim 27.
As to claim 29, as can be seen from Scheme 3, p. 7648, the resulting polymers are polyethers.
As to claim 30, Table 2, p. 7650, shows the polymser having the recited Tg.
As to claim 31, Table 1, p. 7649, shows the polymers of the invention having the recited Mn.
As to claim 32, as can be seen from Scheme 3, p. 7648, the resulting polymers incorporate the recited backbone segments.
As to claim 36, as can be seen from Scheme 3, p. 7648, the resulting polymers lack the recited structural units.
Claim(s) 14, 15, 21, 22 (first instance), 25, 26, 29, 32, and 34-36 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chopda et al., “Synthesis and Characterization of Epoxy methacrylate of (2E, 6E)-Bis(4-hydroxybenzylidene)-4-methycyclohexanone,” J. Polym. Mater. 36(4) 391-399 (2019) (“Chopda”).
As to claim 14, 21, 22 (first instance), 25, 26, Chopda teaches an epoxy methacrylate resin. Chopda teaches the use of (2E,6E)-bis(4-hydroxybenzylidene)-4-methylcyclohexanone (p. 392). This compound meets Formula III where A is aromatic ring, R2 and R3 are organic groups fused in a ring, Z is hydroxyl, n is 0, Y is hydrogen, t is 4, and each R1 is hydrogen. This structure meets Formula III of claim 21 where one R5 is methyl and the other two are hydrogen, and Formula IIIB of claim 22 (first instance). The resulting polymer is deemed equivalent to a polymer of the aforementioned diol and the corresponding diglycidyl ether, followed by methacrylic acid (see synthesis; scheme 1. The corresponding monomeric diglycidyl ether of bis(4-hydroxybenzylidene)-4-methylcyclohexanone as the structure of Formula (IV) of claim 25, where R2 and R3 are organic groups fused in a ring, n is 0, A is aromatic ring, t is 4, each R1 is hydrogen, Z2 is -O-. This also meets Formula (IVA) of claim 26 where one R5 is methyl and the remainder are hydrogen. The resin prior to reaction with methacrylate can be viewed as a polymer of the diol and corresponding diglycidyl ether of the diol.
As to claim 15, the resin contains more than 5 wt % of units equivalent to those derived from the diol.
As to claim 29, As can be seen form Scheme 1, the resulting polymer is a polyether polymer.
As to claim 32, as can be seen from Scheme 1, the polymer has the recited backbone segments.
As to claim 34, Chopda suggests curing epoxy acrylate as a monomer, thus resulting in a polyether acrylate copolymer (p. 392, col. 1).
As to claim 35, Chopda teaches the resulting rein has an acid value (p. 394, Table 1), suggesting some remainder of the methacrylic acid thus the acrylic portion of the cured resin would be expected to contain some carboxylic acid groups.
As to claim 36, the resin of Chopda lacks the recited units.
Claim(s) 14-16, 29, 30, 32, 34, and 36 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 2005/0089793 (“Kang”).
As to claim 14, Kang teaches a polymer derived from the reaction of epichlorohydrin with the diol
PNG
media_image1.png
93
215
media_image1.png
Greyscale
(para. 0051), specifically bis (4,4’-hydroxy)chalcone, which meets Formula (III) where R2 is an organic group, R3 is hydrogen, n is 0, R1 is hydrogen, Z is OH, which is reactive with epichlorohydrin, A is aromatic ring.
As to claim 15, the reaction of the aforementioned diol means that the monomer is well over 5 wt % of the monomers used, given that the diol is considerably heavier than epichlorohydrin.
As to claim 16, Kang teaches applying to a substrate, thus coating (para. 0134).
As to claim 29, the polymer of Kang, as shown in the structure in the abstract is a polyether polymer.
As to claim 30, while Kang does not discuss Tg, Kang teaches a polymer having the same structure as recited, and is presumed therefore to have the recited Tg.
As to claim 32, the polymer of Kang, as shown in the abstract, has the recited backbone segments.
As to claim 34, Kang teaches curing the polymer with acrylates (paras. 0133-0134). Given that the structure of the polymer of Kang is a polyether, it is expected that the polymer is a polyether acrylate copolymer.
As to claim 36, the structure of Kang, abstract, lacks the recited units.
Claim(s) 14-16, 29-32, 36, and 37 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 4,111,907 (“Green”).
As to claim 14, Green teaches a polymer (abstract). Green teaches Example 3, which contains units having the structure
PNG
media_image2.png
52
265
media_image2.png
Greyscale
, which is formed form the diglycidyl ether 1,5—bis(4-glycidyloxyphenyl)-penta-1,4-dien-3-one (11:5-40). While Green does not state the polymer is derived from the specific monomer, rather the glycidyl derivative, this limitation is considered a product by process limitation. The resin, a product of the diglycidyl ether and resacetophenone, is considered equivalent to one derived from the corresponding diol 1,5-bis(4-hydroxyphenyl)- penta-1,4-dien-3-one with the glycidyl ether of resacetophenone. The corresponding diol 1,5-bis(4-hydroxyphenyl)- penta-1,4-dien-3-one meets Formula III, and the resin is thus considered equivalent to a polymer derived from such a compound.
As to claim 15, the units derived from the above structure constitute more than 5 wt % of the polymer.
As to claim 16, Green teaches coating the material on a substrate (8:54-62).
As to claims 29 and 32, the structure of Example 3 is a polyether polymer having the recited backbone segments (abstract, 11:25-35).
As to claim 30, while Green does not discuss the Tg, the polymer is presumed to have the recited Tg, containing mainly the recited units.
As to claim 31, Example 3 is calculated to have Mn in excess of 2000.
As to claim 36, the polymer of Example 3 lacks the recited structural units.
As to claim 37, Example 3 teaches a 30 wt % solution of the composition in cyclohexanone, and therefore meets the recited amount of nonvolatile components, and the amount of the polymer in the resin solids. Example 3 is calculated as having a Mn in excess of 2000. While Green does not discuss the Tg, the polymer is presumed to have the recited Tg, containing mainly the recited units.
Green teaches coating the material on a substrate (8:54-62). While Green does not state that the coating is for a food or beverage container, it is presumed suitable for that intended use.
Allowable Subject Matter
Claim 23 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim 28 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(d) or 35 U.S.C. 112 (pre-AIA ), 4th paragraph, set forth in this Office action as well as to incorporate the limitations of the base claims and intervening claims consistent with the subject matter of claim 28.
The following is a statement of reasons for the indication of allowable subject matter: While the diol of formula III is known (see Galkin reference included with applicant’s IDS dated 16 August 2024), the prior art does not suggest polymers formed from the monomers of Formula IIID or Formula IVC.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KREGG T BROOKS whose telephone number is (313)446-4888. The examiner can normally be reached Monday to Friday 9 am to 5:30 pm.
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, Arrie Reuther can be reached at (571)270-7026. 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.
/KREGG T BROOKS/ Primary Examiner, Art Unit 1764