US 12,448,477 B2
Synthetic method for the preparation of rheological modifying polymers and the use thereof
Joseph A. Paquette, London (CA); Olabode O. Oyeneye, London (CA); Eric D. Landry, London (CA); and Amer Ebied, London (CA)
Assigned to POLYANALYTIK INC.
Appl. No. 17/261,122
Filed by POLYANALYTIK INC., London (CA)
PCT Filed Jul. 17, 2019, PCT No. PCT/CA2019/050989
§ 371(c)(1), (2) Date Jan. 18, 2021,
PCT Pub. No. WO2020/014785, PCT Pub. Date Jan. 23, 2020.
Claims priority of provisional application 62/699,033, filed on Jul. 17, 2018.
Prior Publication US 2021/0317249 A1, Oct. 14, 2021
Int. Cl. C09K 8/80 (2006.01); A61K 8/81 (2006.01); A61K 47/32 (2006.01); C02F 1/56 (2023.01); C08F 293/00 (2006.01); C08J 3/075 (2006.01); C09K 8/588 (2006.01); C09K 8/88 (2006.01); D21H 17/43 (2006.01); D21H 21/10 (2006.01); D21H 21/18 (2006.01); E21B 43/20 (2006.01); E21B 43/267 (2006.01)
CPC C08F 293/005 (2013.01) [A61K 8/817 (2013.01); A61K 47/32 (2013.01); C02F 1/56 (2013.01); C08J 3/075 (2013.01); C09K 8/588 (2013.01); C09K 8/80 (2013.01); C09K 8/882 (2013.01); D21H 17/43 (2013.01); D21H 21/10 (2013.01); D21H 21/18 (2013.01); E21B 43/20 (2013.01); E21B 43/267 (2013.01); A61K 2800/48 (2013.01); C08F 2438/03 (2013.01)] 14 Claims
 
1. A terpolymer resulting from aqueous polymerization of a mixture of:
monomer A, having a water-soluble monoethylenically unsaturated group consisting of R1—(C—C)—(C═O)—N—(R3)—R4 wherein R1 is H;
R3 is H; and
R4 is H;
monomer B, having a monoethylenically unsaturated monomer capable of forming hydrophobically associative bonds in aqueous medium and amenable to aqueous polymerization conditions consisting of R1—(C═C)—(C—O)—N—(R6)—R7 wherein R1 is H;
R6 is A-methoxyisobutyl,
R7 is H; and
monomer C, having an ionic water-soluble monoethylenically unsaturated group, said monomer C consisting of R3—(C—C)—(C—O)—N—(R10)—R11 wherein R3 is H;
R10 is sodium salt of 2-methylpropane-1-sulfonic acid;
R11 is H; and
an iniferter initiated with light selected from the group comprising R1′-(C—S)—S—Z1 or R2′—S—(C═S)—S—Z2 wherein:
R1′ is selected from the group consisting of: methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, t-butoxy, benzyl, phenyl, N-methylaniline,
Z1 is selected from the group consisting of: propanoic acid, propanoate, phenylpropane-2-yl, cyanomethyl, cyanopropan-2-yl,
R2′ is selected from the group consisting of: is a linear or branched alkyl chain having a carbon length between C1-C12, benzyl, phenyl, isobutyronitrile, propanoate, propanoic acid, benzyl isobutyrate, 2-(pyridin-2-yldisulfanyl) ethyl propionate,
Z2 is selected from the group consisting of: propanoate, propanoic acid, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, benzyl, benzyl isobutyrate, polyethyleneglcoylated 2-cyanopropanoic acid.