US 12,459,889 B2
Sulfobetaine monomers, process for preparing same, and uses thereof
Johann Kieffer, Andrezieux Boutheon (FR); Cédrick Favero, Andrezieux Boutheon (FR); Benoît Legras, Andrezieux Boutheon (FR); and Renaud Souzy, Andrezieux Boutheon (FR)
Assigned to SNF GROUP, Andrezieux Boutheon (FR)
Appl. No. 17/756,709
Filed by SNF GROUP, Andrezieux Boutheon (FR)
PCT Filed Dec. 15, 2020, PCT No. PCT/FR2020/052441
§ 371(c)(1), (2) Date May 31, 2022,
PCT Pub. No. WO2021/123599, PCT Pub. Date Jun. 24, 2021.
Claims priority of application No. 1914533 (FR), filed on Dec. 16, 2019.
Prior Publication US 2023/0183174 A1, Jun. 15, 2023
Int. Cl. C09K 8/584 (2006.01); C07C 303/32 (2006.01); C07C 309/15 (2006.01); C08F 220/34 (2006.01); C08F 220/38 (2006.01); C08F 220/56 (2006.01); C09K 8/588 (2006.01); C09K 8/60 (2006.01); C09K 8/68 (2006.01); C09K 23/34 (2022.01); C11D 1/92 (2006.01); D21H 17/45 (2006.01); D21H 21/10 (2006.01)
CPC C07C 309/15 (2013.01) [C07C 303/32 (2013.01); C08F 220/34 (2013.01); C08F 220/387 (2020.02); C08F 220/56 (2013.01); C09K 8/584 (2013.01); C09K 8/588 (2013.01); C09K 8/604 (2013.01); C09K 8/685 (2013.01); C09K 23/34 (2022.01); C11D 1/92 (2013.01); D21H 17/455 (2013.01); D21H 21/10 (2013.01); C07B 2200/13 (2013.01); C08F 2800/10 (2013.01); C08F 2810/20 (2013.01); C09K 2208/28 (2013.01)] 2 Claims
 
1. A process for preparing a sulfobetaine monomer of formula (V) and/or its acid form comprising reacting:
a compound of formula (VI), and
a compound of formula (VII) and/or one of its salts,
optionally in the presence of at least one solubilizing agent of the compound of formula (VII), and
in the presence of at least one solvent, wherein the said solvent is a compound having a melting temperature below 15° C.,
wherein the reaction is carried out with an amount of polymerization inhibitor of between 10 and less than 500 ppm relative to the total mass of the compounds of formulas (VI) and (VII),

OG Complex Work Unit Chemistry
In formulas (V), (VI) and (VII):
R1 and R4 are, independently of each other, —H or —CH3,
R2 and R3 are, independently of each other, a linear C1-C10 alkyl or branched C3-C10 alkyl or linear C2-C10 alkylene group,
R5 is —H, or a linear C1-C22 alkyl or branched C3-C22 alkyl group, or R5 forms with R6 a C4-C10 carbon ring, optionally branched,
R6 is a linear C1-C22 alkyl or branched C3-C22 alkyl group, or R6 forms with R5 a C4-C10 carbon ring, optionally branched,
X1=—COO—, or —CONH— or —CH2—,
X2=—COO— or —CONH—,
n is an integer between 0 and 10,
wherein
the compound of formula (VI) is chosen from dimethylaminopropyl methacrylamide, dimethylaminopropyl acrylamide, allyldimethylamine, diallylmethyl amine, dimethylaminoethyl methacrylate, and dimethylaminoethyl acrylate;
the compound of formula (VII) is 2-acrylamido-2-methylpropane sulfonic acid and/or one of its salts; and
the polymerization inhibitor is mono methyl ether of hydroquinone (MEHQ),
and wherein said process comprises carrying out the following steps:
a1) adding to a stirred reactor at least one compound of the formula (VI), optionally at least one solubilizing agent of the compound of the formula (VII), and the at least one solvent to obtain a pre-reaction mixture;
a2) adding at least one compound of the formula (VII) and/or one of its salts to the pre-reaction mixture;
a3) after reaction, obtaining sulfobetaine monomers of the formula (V) and/or its acid form in the form of a solution;
a4) extracting the compound of the formula (V) in the form of crystals AA;
a5) combining the crystals AA of the compound of formula (V) with an aqueous solution to form a suspension A;
a6) mixing suspension A for a period of between 1 minute and 20 hours;
a7) obtaining a suspension B of crystals BB of the compound of formula (V) in a hydrated form; and
a8) optionally isolating the crystals BB obtained from suspension B.