IP Library Granted Patent US 9,738,594
Granted Patent B2
US 9,738,594 · App. 14/649,361 · Granted Aug 22, 2017

Crystalline particles of salts of glutamic acid N,N-diacetic acid

Inventors: Roy Gérard Doppen (Deventer, NL); Martin Heus (Arnhem, NL); Cornelis Elizabeth Johannus Van Lare (Wijchen, NL)
Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
C07C229/76C07C227/42C07C229/24C11D3/33C07B2200/13
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Quick Facts
Patent No.
US 9,738,594
App. No.
14/649,361
Granted
Aug 22, 2017
Kind
B2
Abstract

The invention relates to a salt of glutamic acid-N,N-diacetic acid (GLDA) of the formula GLDA-Y m H n , wherein m is equal to or more than 0.5 and lower than or equal to 2.5, n+m=4, and wherein Y is a monovalent cation that is not a proton, comprising L-GLDA-Y m H n to D-GLDA-Y m H n in a range between 100:0 and 50:50 (L:D), characterized in that the salt is crystalline, a process to make such crystalline salt, and to uses of such salt, such as, in particular, in detergent compositions.

Claims (18)

1. Salt of glutamic acid-N,N-diacetic acid (GLDA) of the formula GLDA-Y m H n , wherein m is equal to or more than 0.5 and lower than or equal to 2.5, n+m=4, and wherein Y is a monovalent cation that is not a proton, comprising L-GLDA-Y m H n to D-GLDA-Y m H n in a range between 100:0 and 50:50 (L:D), characterized in that the salt is crystalline.

2. Salt of the formula GLDA-Y m H n according to claim 1 , wherein Y is an alkali metal.

3. Salt of the formula GLDA-Y m H n according to claim 1 , wherein m is about 1 and n is about 3.

4. Salt of the formula GLDA-Y m H n according to claim 1 , wherein the salt comprises L-GLDA-Y m H n : D-GLDA-Y m H n between 75:25 and 50:50 (L:D).

5. Process to prepare the salt of the formula GLDA-Y m H n according to claim 1 , comprising:

a first step providing an aqueous solution containing a salt of GLDA and/or GLDA-H 4 ,

a second step ensuring that the pH of the aqueous solution is equal to or more than 1.8 and less than 5 and performing a racemization step to at least partially racemize the salt of GLDA, one step after the other in random order or simultaneously, and

a third step allowing the aqueous solution to crystallize.

6. Process according to claim 5 , wherein the pH of the second step is in the range between 1.8 and 4.8.

7. Process according to claim 5 , wherein the second step includes a concentrating step.

8. Process according to claim 7 , wherein the concentrating step is carried out until the solution has a concentration of equal to or more than 15 wt % up to or equal to 80 wt %, of GLDA-Y m H n based on the weight of the aqueous solution.

9. Process according to claim 5 , wherein the third step comprises crystallization accomplished by a step selected from the group consisting of allowing the solution to stand until the solution crystallizes, cooling, and seeding.

10. Process according to claim 5 , wherein the third step comprises spraying the aqueous solution of the second step on seeding crystals.

11. Process according to claim 5 , wherein the third step is performed at a temperature of equal to or below 30° C.

12. Process according to claim 5 , wherein the process is a continuous process.

13. Process according to claim 5 , comprising an additional step wherein carbonates, silicates, or a combination of carbonates and silicates are added to the resulting product of the third step, so that the pH of an aqueous solution of the resulting product is above 6.

14. Detergent compositions containing the salt of the formula GLDA-Y m H n according to claim 1 , and further comprising at least one component selected from the group consisting of cleaning additives, antiscaling additives, builders, protective colloids, chelating agents, surfactants, corrosion inhibitors, and inorganic or organic acids.

15. Pharmaceutical preparations containing the salt of the formula GLDA-Y m H n according to claim 1 , and further comprising a pharmaceutically acceptable carrier.

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 Jun 3, 2015
From: DOPPEN, ROY GÉRARD; HEUS, MARTIN; VAN LARE, CORNELIS ELIZABETH JOHANNUS
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 035777/0901 →
Priority Claims (1)
EP 12197178 · Dec 14, 2012 · regional
Continuity (2)
Provisional Application 61751398 · Jan 11, 2013
Related Publication 20150353475A1 · Dec 10, 2015