IP Library Granted Patent US 12,486,338
Granted Patent B2
US 12,486,338 · App. 18/007,583 · Granted Dec 2, 2025

Poly alpha-1,6-glucan derivatives and compositions comprising same

Inventors: Zhengzheng Huang (Hockessin, DE); Douglas J. Adelman (Wilmington, DE); Neil Thomas Fairweather (Liberty Town, OH); Kristi Lynn Fliter (Cincinnati, OH); David Good (Cincinnati, OH); Helen S.M. Lu (Wallingford, PA); Weiming Qiu (Wilmington, DE); Gang Si (Newcastle Upon Tyne, GB); Mark Robert Sivik (Cincinnati, OH)
Assignee: NUTRITION & BIOSCIENCES USA 4, INC.
C08B37/0021C11D3/222C11D3/227
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,486,338
App. No.
18/007,583
Granted
Dec 2, 2025
Kind
B2
Abstract

The disclosure relates to poly alpha-1,6-glucan derivatives comprising poly alpha-1,6-glucan substituted with at least one organic group linked to the poly alpha-1,6-glucan through a linkage moiety selected from ether, sulfonyl, carbonate, or carbamoyl/carbamate, and having a degree of substitution of about 0.001 to about 3.0. The 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 glycosidic linkages, and optionally at least 5% of the backbone glucose monomer units have branches via alpha-1,2 and/or alpha-1,3 glycosidic linkages. Compositions comprising a poly alpha-1,6-glucan derivative can be useful in various applications.

Claims (31)

1 . A composition comprising a poly alpha-1,6-glucan derivative that comprises:

(i) poly alpha-1,6-glucan substituted with at least one organic group linked to the poly alpha-1,6-glucan through a linkage moiety selected from —O—, —OSO 2 —, —OCOO—, or —OCONH—/—OCO —;

(ii) a weight-average degree of polymerization of about 5 to about 4000; and

iii) a degree of substitution of about 0.001 to about 3.0;

wherein the poly alpha-1,6-glucan comprises a backbone of glucose monomer units, wherein greater than or equal to 90% of the backbone glucose monomer units are linked via alpha-1,6 glycosidic linkages, at least about 5% of the backbone glucose monomer units have branches via alpha-1,2 glycosidic linkages, less than 1% of the glycosidic linkages of the poly alpha-1,6-glucan are alpha-1,3 glycosidic linkages,

and wherein the poly alpha-1,6-glucan is not substituted with a hydrophilic group.

2 . The composition of claim 1 , wherein the degree of substitution is about 0.01 to about 1.5.

3 . The composition of claim 1 , wherein the degree of substitution is about 0.6.

4 . The composition of claim 1 , wherein the degree of substitution is about 0.2 to about 0.6.

5 . The composition of claim 1 , wherein at least one the linkage moiety is —O—.

6 . The composition of claim 1 , wherein at least one the linkage moiety is —OCONH—/—OCO —, which optionally is —OCONH—.

7 . The poly alpha-1,6-glucan derivative composition of claim 1 , wherein the organic group comprises a C 1 to C 18 alkyl group, a hydroxy alkyl group, a carboxy alkyl group, a C 2 to C 18 alkenyl group, a C 2 to C 18 alkynyl group, a benzyl group, a C 6 to C 20 aryl group, or a polyether comprising repeat units of (—CH 2 CH 2 O—) and/or (—CH 2 CH(CH 3 )O—) wherein the total number of repeat units is in the range of 2 to 100.

8 . The composition of claim 1 , wherein the organic group comprises a C 1 -C 10 alkyl group, a C 1 -C 10 hydroxyl alkyl group, or a polyether comprising repeat units of (—CH 2 CH 2 O—) and/or (—CH 2 CH(CH 3 )O—) wherein the total number of repeat units is in the range of 2 to 100.

9 . The composition of claim 1 , wherein the organic group comprises a benzyl group.

10 . The composition of claim 1 , wherein the organic group comprises a benzyl group substituted with one or more of a halogen, cyano group, ester group, amide group, ether group, C 1 to C 6 alkyl group, aryl group, C 2 to C 6 alkene group, or C 2 to C 6 alkyne group.

11 . The composition of claim 1 , wherein the organic group comprises an alkyl group that is substituted with another alkyl group.

12 . The composition of claim 11 , wherein the organic group comprises 2-ethylhexyl.

13 . The composition of claim 1 , wherein the poly alpha-1,6-glucan derivative has a biodegradability as determined by the Carbon Dioxide Evolution Test Method of at least 10% after 90 days.

14 . The composition of claim 1 , wherein the poly alpha-1,6-glucan derivative has a weight-average degree of polymerization of about 5 to about 500.

15 . The composition of claim 1 , 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.

16 . The composition of claim 1 , further comprising one or more of a detergent builder, complexing agent, polymer, soil release polymer, surfactancy-boosting polymer, bleaching agent, bleach activator, bleaching catalyst, fabric conditioner, clay, foam booster, suds suppressor, anti-corrosion agent, soil-suspending agent, anti-soil re-deposition agent, dye, bactericide, tarnish inhibitor, optical brightener, perfume, saturated or unsaturated fatty acid, dye transfer-inhibiting agent, chelating agent, hueing dye, calcium cation, magnesium cation, visual signaling ingredient, anti-foam, structurant, thickener, anti-caking agent, starch, sand, or gelling agent.

17 . The composition of claim 1 , wherein

(i) the composition further comprises one or more of a perfume, fragrance, flavor, air odor-reducing agent, insect repellent, insecticide, bubble-generating agent, non-woven material, colorant, preservative, antioxidant, emulsifier, emollient, oil, medicament, or suspending agent; and/or

(ii) the composition is a disinfecting product, cleaning product, coating product, wipe, or hard surface cleaner such as for a floor, countertop, table, desk, tub/shower, sink, toilet bowl, door/cabinet handle/panel, or glass/window.

18 . A method for treating a substrate, the method comprising the steps:

(a) providing a composition according to claim 1 ;

(b) contacting the substrate with the composition; and

(c) optionally rinsing the substrate;

wherein the substrate is a textile, fabric, carpet, upholstery, apparel, or surface.

19 . The composition of claim 1 , further comprising a surfactant.

20 . The composition of claim 1 , further comprising an enzyme.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2023
From: ADELMAN, DOUGLAS; HUANG, ZHENGZHENG; LU, HELEN; SIVIK, MARK ROBERT; SI, GANG; FLITER, KRISTI LYNN; GOOD, DAVID; FAIRWEATHER, NEIL THOMAS; QIU, WEIMING
To: NUTRITION & BIOSCIENCES USA 4, INC.; THE PROCTER & GAMBLE COMPANY
Reel/Frame 064029/0962 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2023
From: THE PROCTER & GAMBLE COMPANY
To: NUTRITION & BIOSCIENCES USA 4, INC.
Reel/Frame 064030/0031 →
Continuity (2)
Provisional Application 63037076 · Jun 10, 2020
Related Publication 20230212325A1 · Jul 6, 2023
References Cited (70)
US 2734005A · Novak et al. · 1956 [cited by applicant]
US 2786786A · Novak et al. · 1957 [cited by applicant]
US 5739122A · Schehlmann et al. · 1998 [cited by applicant]
US 5776435A · Gaffar et al. · 1998 [cited by applicant]
US 6013250A · Cannell et al. · 2000 [cited by applicant]
US 6020303A · Cripe et al. · 2000 [cited by applicant]
US 6060443A · Cripe et al. · 2000 [cited by applicant]
US 6139851A · Omura et al. · 2000 [cited by applicant]
US 6280747B1 · Philippe et al. · 2001 [cited by applicant]
US 7000000B1 · O'Brien · 2006 [cited by applicant]
US 8540971B2 · Zaidel et al. · 2013 [cited by applicant]
US 8642757B2 · O'Brien et al. · 2014 [cited by applicant]
US 8796196B2 · Chan et al. · 2014 [cited by applicant]
US 8871474B2 · Payne et al. · 2014 [cited by applicant]
US 9080195B2 · O'Brien et al. · 2015 [cited by applicant]
US 9139718B2 · Paullin et al. · 2015 [cited by applicant]
US 10005850B2 · Kasat et al. · 2018 [cited by applicant]
US 10260053B2 · Paullin et al. · 2019 [cited by applicant]
US 10301604B2 · Li et al. · 2019 [cited by applicant]
US 11905495B2 · Sivik · 2024 [cited by examiner]
US 20040010864A1 · Vic et al. · 2004 [cited by applicant]
US 20120058196A1 · Friesen et al. · 2012 [cited by applicant]
US 20130244287A1 · O'Brien et al. · 2013 [cited by applicant]
US 20130244288A1 · O'Brien et al. · 2013 [cited by applicant]
US 20140179913A1 · Paullin et al. · 2014 [cited by applicant]
US 20150064748A1 · Caimi et al. · 2015 [cited by applicant]
US 20150232785A1 · Paullin · 2015 [cited by examiner]
US 20150368594A1 · Nagy · 2015 [cited by examiner]
US 20170002335A1 · Payne et al. · 2017 [cited by applicant]
US 20170198324A1 · Cheng et al. · 2017 [cited by applicant]
US 20170218093A1 · Cheng et al. · 2017 [cited by applicant]
US 20180021238A1 · Huh et al. · 2018 [cited by applicant]
US 20180237816A1 · Paullin · 2018 [cited by examiner]
US 20180273731A1 · Opietnik et al. · 2018 [cited by applicant]
US 20180282385A1 · Cheng et al. · 2018 [cited by applicant]
US 20180340199A1 · Nagy et al. · 2018 [cited by applicant]
US 20190078062A1 · Li et al. · 2019 [cited by applicant]
US 20190078063A1 · Li et al. · 2019 [cited by applicant]
US 20190112456A1 · Bell et al. · 2019 [cited by applicant]
US 20190185893A1 · Guan et al. · 2019 [cited by applicant]
US 20190276806A1 · Li et al. · 2019 [cited by applicant]
US 20190359734A1 · Qiu et al. · 2019 [cited by applicant]
US 20190390138A1 · Sivik · 2019 [cited by examiner]
US 20200002646A1 · Huang · 2020 [cited by examiner]
US 20200165360A1 · Behabtu et al. · 2020 [cited by applicant]
US 20210253977A1 · Huang · 2021 [cited by examiner]
US 20210388290A1 · Sivik · 2021 [cited by examiner]
US 20210395648A1 · Sivik · 2021 [cited by examiner]
US 20210395649A1 · Sivik · 2021 [cited by examiner]
US 20210395655A1 · DePoot · 2021 [cited by examiner]
US 20230212325A1 · Huang · 2023 [cited by examiner]
US 20230287148A1 · Huang · 2023 [cited by examiner]
US 20230332073A1 · Sivik · 2023 [cited by examiner]
US 20240301325A1 · Burkhart · 2024 [cited by examiner]
AU 2016243411B2 · 2020 [cited by examiner]
EP 3922704A1 · 2021 [cited by examiner]
EP 3926029A1 · 2021 [cited by examiner]
WO 2001007009A1 · 2001 [cited by applicant]
WO 2015183714A1 · 2015 [cited by applicant]
WO 2016160738A2 · 2016 [cited by applicant]
WO 2017091533A1 · 2017 [cited by applicant]
WO WO2019246228A1 · 2019 [cited by examiner]
WO 2021007264A1 · 2021 [cited by applicant]
Naessens et al., “Leuconostoc dextransucrase and dextran: production, properties and applications”, J. Chem. Technol. Biotechnol. 80:845-860. [cited by applicant]
Vuillemin et al., “Characterization of the First alpha-(1-->3) Branching Sucrases of the GH70 Family”, J. Biol Chem. 291:7687-7702; 2016. [cited by applicant]
Heinze et al., “Functional Polymers Based on Dextran”, POLYSACCHARIDES, 2 (Book Series: Advances in Polymer Science), pp. 199-291; 2006. [cited by applicant]
Togo et al., “Synthesis and characterization of dextran ester derivatives and their adhesive propertie”, J. Wood Sci. 65:66; 2019. [cited by applicant]
Larsen, “Dextran prodrugs—structure and stability in relation to therapeutic activity”, Advanced Drug Delivery Reviews 3:103-154; 1989. [cited by applicant]
Hornig et al., “Nanoscale structures of dextran esters”, Carb. Polymers 68:280-286; 2007. [cited by applicant]
International Preliminary Report on Patentability for PCT/US2021/036529 issued Dec. 13, 2022. [cited by applicant]