DETAILED 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 .
Final Rejection
Claims 1-6, 13, 15-16, 19-20, 23-31 are pending. Claim 1 is independent. Claims 30-31 are new. Claims 7-12, 14, 17-18, 21-22 are cancelled. Claims 1 and 13 are amended in the response filed 6/25/2025.
Response to Amendment
The objection of claims 1-6, 13, 15-16, 19-20, 23-29 is withdrawn.
The provisional nonstatutory double patenting rejection of claims 1-6, 13, 15-16, 19-20, 23-29 as being unpatentable over claims 1-13 and 15-19 of copending Application No. 17/351,616 having publication US 2021/0395655 A1 is withdrawn.
The nonstatutory double patenting rejection of claims 1-6, 13, 15-16, 19-20, 23-29 over claims 1-14 of U.S. Patent No. 11,965,147 B2 is withdrawn.
The rejection of claims 1-6, 13, 15-16, 19-20, 23-29 under 35 U.S.C. 102((a)(1)) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Paulin et al. (AU2016243411B2) is withdrawn.
The rejection of claim(s) 1-6, 13, 15-16, 19-20, 23-29 under 35 U.S.C. 102((a)(1)) as anticipated by Huang et al, WO 2018/112187 is withdrawn.
The rejection of claim(s) 1-6, 13, 15-16, 19-20, 23-29 under 35 U.S.C. 103 as obvious over Huang et al, WO 2018/112187 is maintained.
Response to Arguments
Applicant's arguments filed 6/25/2025 have been fully considered but they are not persuasive. Applicants urge that claim 1 as currently amended recites language regarding how the aryl group (Ar) is directly linked to the poly alpha-1,6-glucan via an ester linkage. Contrary to Applicant’s arguments, claim 1 has been copied herein:
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As highlighted, the claim language presented for examination broadly requires substitution with an ester and is not specific for etherification or esterification as argued. Applicant’s acknowledge on page 8 of their remarks, Huang et al. page 41, lines 7-8 teaches the claimed ester substitution copied herein:
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Applicant’s urging that Huang teach an ether link to the ester substituted benzyl and does not teach or suggest esterification of alpha -1,6 glucan with an aryl ester (eg benzoyl) is not on point with the claim language presented for examination is to substitution since none of the claims presented for examination requires the “esterification of alpha -1,6 glucan with an aryl ester” being argued in the remarks. Thus, Applicants arguments are not found commensurate in scope nor pertinent with the claim amendments presented for examination requiring the “…aryl ester group substitutes the hydroxyl group in the original poly alpha 1,6 glucan used to prepare the poly alpha 1,6 glucan ester”. Examiner notes that the claims do not limit the linkages to esters, however, esters are required. Huang et al. is pertinent to the claim language presented for examination for teaching a composition comprising an alpha-1,6-glucan polysaccharide substituted with at least one ester group (see abstract and page 24 lines 20-35), and accordingly the claims are addressed below.
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) 1-6, 13, 15-16, 19-20, 23-30 are rejected under 35 U.S.C. 103 as obvious over Huang et al, WO 2018/112187.
With regard to claim 1, Huang et al. teach a composition comprising a poly alpha-1,6-glucan ester compound that is used interchangeably with the term dextran. On page 20,ln.20.
Specifically with regard to claim 1 (i) substructure -CG-O-CO-Ar, wherein “-CG -” of said substructure represents a carbon of a glucose monomer unit of the poly alpha-1,6-glucan ester compound, “-Ar” represents an aryl group, and “-O-CO-Ar’ represents an aryl ester group, wherein the aryl ester group substitutes for a hydroxyl group that was originally present in a poly alpha-1,6-qlucan used to prepare the poly alpha-1,6-glucan ester compound, Huang et al. teach a composition comprising an alpha-1,6-glucan polysaccharide substituted with at least one ester group (see abstract and page 24 lines 20-35). See also page 11,ln.20-30 teaching the term "aryl" means an aromatic carbocyclic group having a single ring (e.g., phenyl), multiple rings (e.g., biphenyl), or multiple condensed rings in which at least one is aromatic, (e.g., 1,2,3,4-tetrahydronaphthyl, naphthyl, anthryl, or phenanthryl), which is optionally mono-, di-, or trisubstituted with alkyl groups. By aryl is also meant heteroaryl groups where heteroaryl is defined as 5-, 6-, or 7-membered aromatic ring 25 systems having at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur. Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrrolyl, pyrazolyl, pyrazinyl, pyridazinyl, oxazolyl, furanyl, quinolinyl, isoquinolinyl, thiazolyl, and thienyl, which can optionally be substituted with alkyl groups.
Specifically with regard to claim 1 (ii) a weight-average degree of polymerization of about 5 to about 1000; Huang et al. teach that the polysaccharide has a degree of polymerization of 5-1400 (see page 3, lines 31-32 and prior art claim 14) meets the claim 1ii limitation to a degree of polymerization of at least 5.
Specifically with regard to claim 1 (iii) | a degree of substitution with the aryl ester group of about 0.01 to about 1.5, Huang et al. teaches the limitations that the polysaccharide has a degree of substitution of 0.001-3.0 (see page 3, line 33-page 4, line 1), meeting the claim 1iii.
Claim 1 limitation to wherein greater than or equal to 90% of the backbone glucose monomer units are linked via alpha-1,6 glycosidic linkages is encompassed by Huang claim 4 on page 76 teaching poly alpha-1,6-glucan comprises a backbone of glucose monomer units wherein greater than or equal to 40% of the glucose monomer units are linked via alpha-1,6-glycosodic linkages. And see page 21, line 11, teaching dextran long chains can have at least about 98% alpha 1,6 glycosidic linkages.
Claim 1 limitation to wherein at least about 5% of the backbone glucose monomer units have branches via alpha-1,2 glycosidic linkages, is suggested by Huang et al. page 2,ln.23-24 that the poly alpha-1,6-glucan has a degree of alpha-1,2-branching that is less than 50%. And see page 22, ln.1-3 teaching the poly-alpha-1,6 glucan has less than or equal to 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1%, or 0% (or any integer value between 0% and 50%) of short branching, for example alpha-1,2- branching.
Huang et al. teach less than 1% alpha-1,3 glycosidic linkages of the glycosidic linkages of the poly alpha-1,6-glucan since suitable polysaccharides include dextran, which contains at least 95% of alpha-1,6 linkages with side chains of alpha 1,3-glucan (see page 20, lines 11-18), teaching insoluble poly alpha-1,3-glucan in some embodiments can be in the form of a copolymer (e.g., graft copolymer) having (i) a backbone comprising dextran (e.g., with at least about 95%, 96%, 97%, 98%, 99%, or 100% alpha-1,6 linkages) thus, if there are 100% alpha-1,6 linkages, this dextran reads upon claim language to less than 1% alpha 1,3 glycosidic linkages.
Claim 2 limitation to wherein at least about 15% of the backbone glucose monomer units have branches via alpha-1,2 glycosidic linkages is read upon by Huang et al. page 2,ln.23-24 teaching that the poly alpha-1,6-glucan has a degree of alpha-1,2-branching that is less than 50%. And see page 22, ln.1-3 teaching the poly-alpha-1,6 glucan has less than or equal to 50%, 40%, 30%, 20%, 10%, 5%, 4%, 3%, 2%, 1%, or 0% (or any integer value between 0% and 50%) of short branching, for example alpha-1,2- branching.
Claim 3 limitation to wherein the poly alpha-1,6- glucan is further substituted with an acyl group -CO-R’, wherein R” comprises a chain of 1 to 24 carbon atoms is taught by Huang et al. teaching suitable aryl ester groups comprise a C1-18 alkyl group and a benzylating group (see page 41, lines 5-10).
Claim 4 limitation to wherein the aryl ester group comprises a benzoyl group is met by Huang et al page 41, lines 5-10, meeting claim benzoyl group substitution because page 41, lines 5-10 teach a carbonyl group C=O attached to a benzyl in line 9, which meets the claim language to a benzoyl group.
Claim 5 limitation to wherein the aryl ester group comprises a benzoyl group substituted with at least one halogen, alkyl, halogenated alkyl, ether, cyano, or aldehyde group is met by Huang et al page 41, lines 1-12, copied herein
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Claim 6 limitation to wherein the acyl group -CO-R” is an acetyl group or a propionyl group, is met by Huang et al. teaching the glucan can be derivatized with aа carboxymethyl group by contacting poly alpha-1,3-glucan, poly alpha-1,6-glucan, or poly alpha-1,3-1,6-glucan with monochloroacetic acid under alkaline conditions. Etherification agents suitable for preparing a carboxyalkyl poly glucan ether compound may include haloalkylates (e.g., chloroalkylate). Examples of haloalkylates include haloacetate (e.g., chloroacetate), 3- halopropionate (e.g., 3-chloropropionate) and 4-halobutyrate (e.g., 4-chlorobutyrate). For example, chloroacetate (monochloroacetate) (e.g., sodium chloroacetate) can be used as an etherification agent to prepare carboxymethyl poly alpha-1,3-glucan or carboxymethyl poly alpha-1,6-glucan. See page 36,ln.25-page 37,ln.5.
Claim 13 limitation to wherein the degree of substitution with the aryl ester group is about 0.01 to about 0.6, is met by page 3, line 33-page 4, line 1 Huang et al. teach the limitations that the polysaccharide has a degree of substitution of 0.001-3.0.
Claim 15 limitation to wherein the poly alpha-1,6- glucan ester compound has a weight-average degree of polymerization of about 5 to about 500 is met by page 18 line 14 teaching the range of 5-500.
Although Huang et al is silent with respect to the biodegradability value of their polysaccharides as required in claim16, the examiner asserts that the polysaccharides disclosed in Huang et al would inherently meet the biodegradability requirements of the instant invention, since products of identical chemical composition cannot have mutually exclusive properties, absent a showing otherwise.
Claim 19 limitation to being in the form of a liquid, gel, powder, hydrocolloid, aqueous solution, granule, tablet, capsule, bead or pastille, single compartment sachet, pad, multi-compartment sachet, single compartment pouch, or multi-compartment pouch is met by Huang et al. page 4,ln.4-8 teaching the composition is in the form of a liquid, gel or pouch (see page 4, lines 4-7),
Instant claim 20 is met by the prior art claim 18.
And product of clam 23 is met by the examples and page 1,ln.25-30.
Huang et al. teach claims 25-26 to DPw (weight average degree of polymerization) on page 3, lines 32.
Huang et al. teach their composition further contains surfactants and enzymes, such as amylase (see page 4, lines 8-21), meeting instant claims 27-29. Specifically, Huang et al. page 4,ln.8-18 teaching the composition further comprises at least one of a surfactant, an enzyme, a detergent builder, a complexing agent, a polymer, 10 a soil release polymer, a surfactancy-boosting polymer, a bleaching agent, a bleach activator, a bleaching catalyst, a fabric conditioner, a clay, a foam booster, a suds suppressor, an anti-corrosion agent, a soil-suspending agent, an anti-soil re-deposition agent, a dye, a bactericide, a tarnish inhibitor, an optical 15 brightener, a perfume, a saturated or unsaturated fatty acid, a dye transfer inhibiting agent, a chelating agent, a hueing dye, a calcium cation, a magnesium cation, a visual signaling ingredient, an anti-foam, a structurant, a thickener, an anti-caking agent, a starch, sand, a gelling agent, or a combination thereof.
Huang et al. teach a composition comprising an alpha-1,6-glucan polysaccharide substituted with at least one ester group (see abstract and page 24 lines 20-35) and see page 11,ln.20-30 teaching the term "aryl" means an aromatic carbocyclic group having a single ring (e.g., phenyl), multiple rings (e.g., biphenyl), or multiple condensed rings in which at least one is aromatic, (e.g., 1,2,3,4-tetrahydronaphthyl, naphthyl, anthryl, or phenanthryl), which is optionally mono-, di-, or trisubstituted with alkyl groups. By aryl is also meant heteroaryl groups where heteroaryl is defined as 5-, 6-, or 7-membered aromatic ring 25 systems having at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur. Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrrolyl, pyrazolyl, pyrazinyl, pyridazinyl, oxazolyl, furanyl, quinolinyl, isoquinolinyl, thiazolyl, and thienyl, which can optionally be substituted with alkyl groups meeting new claim 30.
Huang et al. teach that the hydrophobic group is linked to the polysaccharide through an ether moiety or a carbamate moiety (see page 14, lines 10-18), and while the composition of Huang et al. has at least one hydrophilic group, with respect to new claim 31, one of ordinary skill is guided by page 12,ln.22, to remove the hydrophilic group if repelling soil is of no concern because the amphiphilic group may function as soil release. See page 12, guiding one of ordinary skill to the reasons to include or exclude certain groups in the polysaccharide.
Huang et al. do not exemplify the claimed composition However, it would have nonetheless been obvious to the skilled artisan to produce the claimed composition, as the reference teaches each of the claimed ingredients within the claimed proportions for the same utility.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/PREETI KUMAR/Examiner, Art Unit 1761
/ANGELA C BROWN-PETTIGREW/Supervisory Patent Examiner, Art Unit 1761
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