IP Library Granted Patent US 9,637,868
Granted Patent B2
US 9,637,868 · App. 14/437,228 · Granted May 2, 2017

Phosphated compounds as adhesion promoters

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Quick Facts
Patent No.
US 9,637,868
App. No.
14/437,228
Granted
May 2, 2017
Kind
B2
Abstract

A bitumen containing composition, comprising bitumen and a phosphate compound, which is obtainable by the esterification of a polyhydric alcohol having at least three hydroxyl groups, with a carboxylic acid having 8-24 carbon atoms, preferably 12-22 carbon atoms, or a derivative thereof, wherein at least one but not all of the hydroxyl groups are esterified, provided that when the polyhydric alcohol has 5 or more hydroxyl groups then at least two but not all of the hydroxyl groups are esterified, followed by reacting the ester obtained with a phosphatising reagent; wherein the said composition is not a bitumen-in-water emulsion.

Claims (33)

1. A bitumen containing composition comprising bitumen and a phosphate compound, the phosphate compound prepared by the esterification of a polyhydric alcohol having at least three hydroxyl groups, with a carboxylic acid having 8-24 carbon atoms, or a derivative thereof, wherein at least one but not all of the hydroxyl groups are esterified, provided that when the polyhydric alcohol has 5 or more hydroxyl groups, then at least two but not all of the hydroxyl groups are esterified, followed by reacting the ester obtained with a phosphatising reagent;

wherein the said composition is not a bitumen-in-water emulsion.

2. The composition according to claim 1 , wherein the phosphated compound has the formula:

where Z=—PO 3 H, H or R—(C═O)—, where R—(C═O)— is an acyl group having 8-24 carbon atoms; and n=0-3; provided that at least one Z is R—(C═O)— and at least one Z is —PO 3 H, provided that when n=2 or 3 then at least two Z is R—(C═O)—;

or the formula:

where X=—CH 2 O—Z or —CH 2 CH 3 ; Z has the same meaning as in formula I; and

provided that at least one Z is —PO 3 H and at least one Z is R—(C═O)—.

3. The composition according to claim 2 , wherein in formula (I), n=0.

4. The composition according to claim 2 , wherein in formula (I), n=3.

5. The composition according to claim 2 , wherein in formula (II), X is CH 2 O—Z and Y is Z.

6. The composition according to claim 2 , wherein in formula (II), X is —CH 2 CH 3 and

7. The composition according to claim 3 , wherein said phosphate compound is prepared by the steps of transesterification of a triglyceride with glycerol, followed by reaction with a phosphatising reagent.

8. The composition according to claim 1 , further comprising less than 5 wt % water.

9. The composition according to claim 8 , wherein the phosphate compound is 0.05 to 5% by weight, based on the amount of bitumen.

10. A method for strengthening adhesion between bitumen and aggregates comprising the step of:

adding the bitumen containing composition of claim 1 to the said aggregates.

11. An asphalt composition comprising the bitumen containing composition of claim 1 and aggregates.

12. The asphalt composition according to claim 11 , comprising from 1 to 25% by weight of the bitumen, and 75 to 99% by weight of the aggregates.

13. A method for paving a road, a sidewalk, a parking lot or an airport runway comprising the step of:

applying the asphalt composition of claim 11 to a road surface, a sidewalk surface, parking lot surface, or an airport runway surface.

14. The method according to claim 13 , wherein the paying method is a hot-mix or warm-mix paving procedure.

15. A method for paving comprising the steps of:

mixing the bitumen composition of claim 1 with aggregates to form a mixture having a temperature of 100-190° C.; and

applying said mixture to a surface.

16. The bitumen containing composition of claim 1 , wherein the carboxylic acid has 12-22 carbon atoms.

17. A method for strengthening adhesion between bitumen and aggregates comprising the step of:

adding the phosphated compound of claim 1 to the aggregates to form a phosphate compound-aggregate mixture, and thereafter adding the bitumen to the phosphated compound-aggregate mixture.

18. The method of claim 15 , further comprising the step of compacting said mixture after it was applied to the surface.

19. A bitumen containing composition comprising bitumen and a phosphate compound, the phosphate compound prepared by the esterification of a polyhydric alcohol having at least three hydroxyl groups, with a carboxylic acid having 8-24 carbon atoms, or a derivative thereof, wherein at least one but not all of the hydroxyl groups are esterified, provided that when the polyhydric alcohol has 5 or more hydroxyl groups, then at least two but not all of the hydroxyl groups are esterified, followed by reacting the ester obtained with a phosphatising reagent, and wherein the phosphated compound has the formula:

where Z=—PO 3 H, H or R—(C═O)—, where R—(C═O)— is an acyl group having 8-24 carbon atoms; and n=0-3; provided that at least one Z is R—(C═O)— and at least one Z is —PO 3 H, provided that when n=2 or 3 then at least two Z is R—(C═O)—;

or the formula:

where X=—CH 2 O═Z or —CH 2 CH 3 ; Z has the same meaning as in formula I; and

provided that at least one Z is —PO 3 H and at least one Z is R—(C═O)—, and further wherein where n=0 in formula (I), the phosphate compound is prepared by the steps of transesterification of a triglyceride with glycerol, followed by reaction with a phosphatising reagent, and further wherein the composition comprises less than 5 wt % water, and further wherein bitumen is present in an amount of greater than 90 wt %.

Assignments (4)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
CHANGE OF ADDRESS Recorded May 15, 2017
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 042745/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2015
From: NORDBERG, JOHAN; HAGBERG, DANIEL; GOROCHOVCEVA, NATALIJA
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 035455/0733 →