IP Library Granted Patent US 10,787,524
Granted Patent B2
US 10,787,524 · App. 15/550,883 · Granted Sep 29, 2020

Oxidized dextran

Inventors: Jayme L. Paullin (Claymont, DE); Rakesh Nambiar (West Chester, PA)
Assignee: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
C08B37/0021A23L29/273A61K31/721C08B31/18C08L5/02C11D3/0036C11D3/223C12N9/1048A23V2002/00
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Quick Facts
Patent No.
US 10,787,524
App. No.
15/550,883
Granted
Sep 29, 2020
Kind
B2
Abstract

Compositions comprising oxidized dextran compounds are disclosed herein. Oxidized dextran compounds are produced by contacting dextran under aqueous conditions with at least one N-oxoammonium salt, at least one periodate compound, and/or at least one peroxide compound.

Claims (66)

1. A composition comprising an oxidized dextran compound, wherein the oxidized dextran compound is produced by contacting dextran under aqueous conditions with at least one N-oxoammonium salt, at least one periodate compound, and/or at least one peroxide compound, wherein the dextran consists of:

(i) about 87-91.5 wt % glucose linked only at positions 1 and 6;

(ii) about 0.1-1.2 wt % glucose linked only at positions 1 and 3;

(iii) about 0.1-0.7 wt % glucose linked only at positions 1 and 4;

(iv) about 7.7-8.6 wt % glucose linked only at positions 1, 3 and 6; and

(v) about 0.4-1.7 wt % glucose linked only at:

(a) positions 1, 2 and 6, or

(b) positions 1, 4 and 6;

wherein the weight-average molecular weight (Mw) of the dextran is about 50 million to 200 million Daltons and the z-average radius of gyration of the dextran is about 200-280 nm.

2. The composition of claim 1 , wherein the dextran consists of:

(i) about 89.5-90.5 wt % glucose linked only at positions 1 and 6;

(ii) about 0.4-0.9 wt % glucose linked only at positions 1 and 3;

(iii) about 0.3-0.5 wt % glucose linked only at positions 1 and 4;

(iv) about 8.0-8.3 wt % glucose linked only at positions 1, 3 and 6; and

(v) about 0.7-1.4 wt % glucose linked only at:

(a) positions 1, 2 and 6, or

(b) positions 1, 4 and 6.

3. The composition of claim 1 , wherein the dextran is a product of a glucosyltransferase enzyme comprising an amino acid sequence that is at least 90% identical to SEQ ID NO:1 or SEQ ID NO:2.

4. The composition of claim 1 , wherein the dextran is contacted with the periodate compound.

5. The composition of claim 1 , wherein the dextran is first contacted with the periodate compound, and then contacted with the N-oxoammonium salt.

6. The composition of claim 1 , wherein the N-oxoammonium salt comprises a TEMPO oxoammonium salt.

7. The composition of claim 1 , wherein the composition is a household product, personal care product, industrial product, pharmaceutical product, or food product.

8. The composition of claim 1 , wherein the composition is a detergent composition present in a household product.

9. A method of producing an oxidized dextran compound, the method comprising:

contacting dextran under aqueous conditions with at least one N-oxoammonium salt, at least one periodate compound, and/or at least one peroxide compound, wherein the dextran consists of:

(i) about 87-91.5 wt % glucose linked only at positions 1 and 6;

(ii) about 0.1-1.2 wt % glucose linked only at positions 1 and 3;

(iii) about 0.1-0.7 wt % glucose linked only at positions 1 and 4;

(iv) about 7.7-8.6 wt % glucose linked only at positions 1, 3 and 6; and

(v) about 0.4-1.7 wt % glucose linked only at:

(a) positions 1, 2 and 6, or

(b) positions 1, 4 and 6;

wherein the weight-average molecular weight (Mw) of the dextran is about 50 million to 200 million Daltons and the z-average radius of gyration of the dextran is about 200-280 nm;

wherein the dextran is oxidized by the N-oxoammonium salt, periodate compound, and/or peroxide compound thereby producing the oxidized dextran compound.

10. The method of claim 9 , wherein:

(I) the dextran is contacted with the periodate compound; or

(II) the dextran is first contacted with the periodate compound, and then contacted with the N-oxoammonium salt.

11. The method of claim 9 , wherein the N-oxoammonium salt comprises:

(I) a TEMPO oxoammonium salt, or

(II) a 4-acetamido-TEMPO oxoammonium salt.

12. A method of increasing the builder capacity and/or anti-redeposition capacity of an aqueous composition, wherein the method comprises:

contacting an oxidized dextran compound produced according to the method of claim 9 with the aqueous composition, wherein the builder and/or anti-redeposition capacity of the aqueous composition is increased by the oxidized dextran compound compared to the builder and/or anti-redeposition capacity of the aqueous composition before the contacting step.

13. A method of treating a material, said method comprising:

contacting the material with an aqueous composition comprising an oxidized dextran compound produced according to the method of claim 9 .

14. The method of claim 9 , wherein the dextran is a product of a glucosyltransferase enzyme comprising an amino acid sequence that is at least 90% identical to SEQ ID NO:1 or SEQ ID NO:2.

15. The method of claim 14 , wherein the dextran is a product of a glucosyltransferase enzyme comprising an amino acid sequence that is at least 95% identical to SEQ ID NO:1 or SEQ ID NO:2.

16. The method of claim 9 , further comprising isolating the oxidized dextran compound.

17. The method of claim 11 , wherein the TEMPO oxoammonium salt or the 4-acetamido-TEMPO oxoammonium salt is provided by oxidizing an agent comprising TEMPO under said aqueous conditions.

18. The composition of claim 1 , wherein the composition is a detergent composition.

19. The composition of claim 3 , wherein the dextran is a product of a glucosyltransferase enzyme comprising an amino acid sequence that is at least 95% identical to SEQ ID NO:1 or SEQ ID NO:2.

20. The composition of claim 1 , wherein the dextran consists of:

(i) 87-91.5 wt % glucose linked only at positions 1 and 6;

(ii) 0.1-1.2 wt % glucose linked only at positions 1 and 3;

(iii) 0.1-0.7 wt % glucose linked only at positions 1 and 4;

(iv) 7.7-8.6 wt % glucose linked only at positions 1, 3 and 6; and

(v) 0.4-1.7 wt % glucose linked only at:

(a) positions 1, 2 and 6, or

(b) positions 1, 4 and 6.

21. The composition of claim 20 , wherein the dextran consists of:

(i) 89.5-90.5 wt % glucose linked only at positions 1 and 6;

(ii) 0.4-0.9 wt % glucose linked only at positions 1 and 3;

(iii) 0.3-0.5 wt % glucose linked only at positions 1 and 4;

(iv) 8.0-8.3 wt % glucose linked only at positions 1, 3 and 6; and

(v) 0.7-1.4 wt % glucose linked only at:

(a) positions 1, 2 and 6, or

(b) positions 1, 4 and 6.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2020
From: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
To: NUTRITION & BIOSCIENCES USA 4, INC.
Reel/Frame 055028/0496 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ENTITY TYPE PREVIOUSLY RECORDED AT REEL: 049879 FRAME: 0043. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 6, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 050300/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT INDUSTRIAL BIOSCIENCES USA, LLC
Reel/Frame 049879/0043 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2018
From: PAULLIN, JAYME L; NAMBIAR, RAKESH
To: E I DU PONT DE NEMOURS AND COMPANY
Reel/Frame 045435/0090 →