Hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid

Patent metadata

Field	Value
Publication number	US-11535587-B2
Application number	US-202217664208-A
Country	US
Kind code	B2
Filing date	May 19, 2022
Priority date	Mar 20, 2017
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The present invention relates to a hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid having a 2-theta powder X-ray diffraction diagram comprising peaks at 10.58°, 11.2°, 12.65°, 13.66°, 16.28°, 18.45°, 20°, 20.4°, 22.5°, 25.5°, 25.88°, 26.47°, 28.52°, 30.28°, 30.8°, 34.09°, 38.19°, 40.69°, 41.82°, 43.74°, 46.04° degrees (+/−0.1°).The present invention also relates to a production method for this form of 2-acrylamido-2-methylpropane sulfonic acid and a preparation method for an aqueous solution A of a salt of this form of 2-acrylamido-2-methylpropane sulfonic acid, and the (co)polymer of this form of -acrylamido-2-methylpropane sulfonic acid.

First claim

The invention claimed is:

1. A preparation method of an aqueous solution A of a 2-acrylamido-2-methylpropane sulfonic acid salt, comprising the following steps:
a) preparing an aqueous solution X of a hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid having a 2-theta powder X-ray diffraction diagram comprising peaks at 10.58°, 11.2°, 12.65°, 13.66°, 16.28°, 18.45°, 20°, 20.4°, 22.5°, 25.5°, 25.88°, 26.47°, 28.52°, 30.28°, 30.8°, 34.09°, 38.19°, 40.69°, 41.82°, 43.74°, and 46.04° degrees, all peak values being +/−0.1,
b) putting in contact and mixing the aqueous solution X with a compound Y chosen from an alkali or alkaline earth metal hydroxide, an alkali or alkaline earth metal oxide, ammonia, an amine having the following formula NR 1 R 2 R 3 or an alkali or alkaline earth metal carbonate, wherein R 1 , R 2 and R 3 are hydrocarbon groups, thereby forming the solution A comprising the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid salt.

2. The method according to claim 1 , wherein R 1 , R 2 and R 3 are alkyl groups.

3. The method according to claim 1 , wherein the molar ratio between 2-acrylamido-2-methylpropane sulfonic acid and compound Y is between 1:0.1 and 1:1.1.

4. The method according to claim 1 , wherein the aqueous solution X has a 2-acrylamido-2-methylpropane sulfonic acid concentration between 1 and 700 g/L, and wherein the molar ratio between 2-acrylamido-2-methylpropane sulfonic acid and compound Y is between 1:0.5 and 1:1.05.

5. The method according to claim 1 , wherein compound Y is ammonia.

6. The method according to claim 1 , wherein compound Y is an aqueous solution of an alkali or alkaline earth metal hydroxide.

7. The method according to claim 1 , wherein compound Y is sodium hydroxide.

8. The method according to claim 1 , wherein at least one polymerization inhibitor is added during the preparation of solution A, wherein the at least one polymerization inhibitor is selected from the group consisting of hydroquinone, paramethoxyphenol, phenothiazine, 2,2,6,6-tetramethyl(piperidin-1-yl)oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, phenylene diamine derivatives, mixtures thereof.

9. The method according to claim 1 , wherein at least one polymerization inhibitor is added during the preparation of solution A, wherein the at least one polymerization inhibitor is paramethoxyphenol.

10. The method according to claim 1 , wherein, during the mixing of aqueous solution X with aqueous solution Y, the temperature is maintained between −10 and 60° C.

11. The method according to claim 1 , wherein, during the mixing of aqueous solution X with aqueous solution Y, the temperature is maintained between 0 and 30° C.

12. The method according to claim 1 , wherein the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid presents a Fourier transform infrared spectrum comprising peaks at 3280 cm −1 , 3126 cm −1 , 1657 cm −1 , 1595 cm −1 , 1453 cm −1 , 1395 cm −1 , 1307 cm −1 , 1205 cm −1 , 1164 cm −1 , 1113 cm −1 , 1041 cm −1 , 968 cm −1 , 885 cm −1 , 815 cm −1 , and 794 cm −1 , all peak values being +/−8 cm −1 .

13. The method according to claim 1 , wherein the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid presents minimum ignition energy greater than 400 mJ.

14. The method according to claim 1 , wherein the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid presents 4 thermal phenomena with the Differential Scanning Calorimetry technique at 70° C., 100° C., 150° C. and 190° C., all +/−10° C.

15. The method according to claim 1 , wherein the hydrated crystalline form of 2-acrylamido-2-methylpropane sulfonic acid has a water/2-acrylamido-2-methylpropane sulfonic acid molar ratio of 1:1.

Assignees

• Spcm Sa

Inventors

• Favero Cédrick
• Kieffer Johann

Classifications

• C02F1/56

  Macromolecular compounds · CPC title

• C09K8/68

  containing organic compounds · CPC title

• C09K8/588

  characterised by the use of specific polymers {(polymeric surfactants C09K8/584)} · CPC title

• C02F2103/10

  from quarries or from mining activities · CPC title

• C07C309/15 Primary

  the nitrogen atom of at least one of the amino groups being part of any of the groups [IMAGE cpc-sch-C07C-0975.gif], X being a hetero atom, Y being any atom · CPC title