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

Patent metadata

Field	Value
Publication number	US-11535588-B2
Application number	US-202217664209-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 (co)polymer of 2-acrylamido-2-methylpropanesulfonic acid, in its acidic and/or salified form,
wherein at least a portion of the 2-acrylamido-2-methylpropanesulfonic acid is in hydrated crystalline form and has a powder X-ray diffraction pattern including 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 2-theta, all peak values being +/−0.1°.

2. The (co)polymer according to claim 1 , wherein the (co)polymer comprises one or more additional monomers selected from the group consisting of non-ionic monomers, cationic monomers, zwitterionic monomers, anionic monomers distinct from 2-acrylamido-2-methylpropanesulfonic acid being in hydrated crystalline form and having a powder X-ray diffraction pattern including 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 2-theta, all peak values being +/−0.1°, and mixtures thereof.

3. The (co)polymer according to claim 1 , wherein the (co)polymer is a copolymer of the hydrated crystalline form of 2-acrylamido-2-methylpropanesulfonic acid and at least one non-ionic monomer.

4. The (co)polymer according to claim 1 , wherein the (co)polymer is a copolymer of the hydrated crystalline form of 2-acrylamido-2-methylpropanesulfonic acid and at least one non-ionic monomer selected from the group consisting of acrylamide; N-isopropylacrylamide; N,N-dimethylacrylamide; N-vinylformamide; acryloyl morpholine; N,N-diethyl acrylamide; N-tert-butyl acrylamide; N-tert-octylacrylamide;
N-vinylpyrrolidone; N-vinylcaprolactam; N-vinyl-imidazole, hydroxyethyl methacrylamide, hydroxypropylacrylate, isoprenoln diacetone acrylamide, and mixture thereof.

5. The (co)polymer according to claim 2 , wherein the anionic monomer is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, acrylamide undecanoic acid, acrylamide 3-methylbutanoic acid, maleic anhydride; vinylsulfonic acid, vinylphosphonic acid, allylsulfonic acid, methallylsulfonic acid, 2-methylidenepropane-1,3-disulfonic acid, 2-sulfoethylmethacrylate, sulfopropylmethacrylate, sulfopropylacrylate, allylphosphonic acid, styrene sulfonic acid, 2-acrylamido-2-methypropane disulfonic acid, salts of these monomers, and mixture thereof.

6. The (co)polymer according to claim 2 , wherein the cationic monomer is selected from the group consisting of quaternized dimethylaminoethyl acrylate, quaternized dimethylaminoethyl methacrylate, dimethyldiallylammonium chloride, acrylamido propyltrimethyl ammonium chloride, methacrylamido propyltrimethyl ammonium chloride, and mixture thereof.

7. The (co)polymer according to claim 2 , wherein the zwitterionic monomer is selected from the group consisting of 2-((2-(acryloyloxy)ethyl) dimethylammonio) ethane-1-sulfonate, 3-((2-(acryloyloxy)ethyl) dimethylammonio) propane-1-sulfonate, 4-((2-(acryloyloxy)ethyl) dimethylammonio) butane-1-sulfonate, [2-(acryloyloxy)ethyl)] (dimethylammonio) acetate, 2-((2-(methacryloyloxy) ethyl) dimethylammonio) ethane-1-sulfonate, 3-((2-(methacryloyloxy) ethyl) dimethylammonio) propane-1-sulfonate, 4-((2-(methacryloyloxy) ethyl) dimethylammonio) butane-1-sulfonate, [2-(methacryloyloxy)ethyl] (dimethylammonio) acetate, 2-((3-acrylamidopropyl) dimethylammonio) ethane-1-sulfonate, 3-((3-acrylamidopropyl) dimethylammonio) propane-1-sulfonate, 4-((3-acrylamidopropyl) dimethylammonio) butane-1-sulfonate, [3-(acryloyloxy) propyl] (dimethylammonio) acetate, 2-((3-methacrylamidopropyl) dimethylammonio) ethane-1-sulfonate, 3-((3-methacrylamidopropyl) dimethylammonio) propane-1-sulfonate, 4-((3-methacrylamidopropyl) dimethylammonio) butane-1-sulfonate, [3-(methacryloyloxy)propyl)] (dimethylammonio) acetate, and mixture thereof.

8. The (co)polymer according to claim 1 , wherein the (co)polymer is linear, structured or crosslinked.

9. The (co)polymer according to claim 1 , wherein the (co)polymer comprises at least one LCST group.

10. The (co)polymer according to claim 1 , wherein the (co)polymer comprises at least one UC ST group.

11. The (co)polymer according to claim 1 , wherein the (co)polymer has an average molecular weight by weight of between 1 and 40 millions g/mol.

12. The (co)polymer 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 (co)polymer 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 (co)polymer 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 (co)polymer 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

• C08F20/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloylmorpholine} · CPC title

• C09K8/588

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

• C07C303/02

  of sulfonic acids or halides thereof · CPC title

• C07C303/44

  Separation; Purification · CPC title