US 12,410,118 B2
Glycerol (meth)acrylate carboxylic ester having a long shelf life
Patrik Hartmann, Buettelborn (DE); Marita Kaufmann, Griesheim (DE); Steffen Krill, Mühltal (DE); Thorben Schütz, Alsbach-Hähnlein (DE); Marcel Treskow, Darmstadt (DE); and Andrea Wittkowski, Gross-Umstadt (DE)
Assigned to Evonik Operations GmbH, Essen (DE)
Filed by Evonik Operations GmbH, Essen (DE)
Filed on May 22, 2022, as Appl. No. 17/750,383.
Application 17/750,383 is a division of application No. 16/479,497, granted, now 11,414,373, previously published as PCT/EP2017/079124, filed on Nov. 14, 2017.
Claims priority of application No. 17152399 (EP), filed on Jan. 20, 2017.
Prior Publication US 2022/0281801 A1, Sep. 8, 2022
Int. Cl. C07C 69/732 (2006.01)
CPC C07C 69/732 (2013.01) 16 Claims
 
1. A storage stable composition, comprising:
a) glycerol (meth)acrylate carboxylic esters selected from the group consisting of Formula (I) A, Formula (I) B and mixtures thereof, wherein, structurally, Formula (I) A and Formula (I) B are:

OG Complex Work Unit Chemistry
and wherein:
R1 is selected from the group consisting of H and CH3;
R2 is selected from the group consisting of: hydrogen; a C1 to C30 aliphatic group optionally with a hydroxyl substituent; an aliphatic cyclic group with a C4 to C8 ring unsubstituted or substituted by N, S, O, or P; a C1 to C8 halogenated aliphatic group; an aromatic group having a ring with five or six carbons and optionally with a hydroxyl substituent; a heteroaromatic group substituted by N, S, O or P and having a ring with five or six carbons; and a C2 to C30 unsaturated aliphatic group;
b) carboxylic acids of formula (II):

OG Complex Work Unit Chemistry
wherein R2 is hydrogen; a C1 to C30 aliphatic group optionally with a hydroxyl substituent; an aliphatic cyclic group with a C4 to C8 ring unsubstituted or substituted by N, S, O, or P; a C1 to C8 halogenated aliphatic group; an aromatic group having a ring with five or six carbons and optionally with a hydroxyl substituent; a heteroaromatic group substituted by N, S, O or P and having a ring with five or six carbons; or a C2 to C30 unsaturated aliphatic group; and
c) glycidyl (meth)acrylate;
d) optionally, Broensted acids;
wherein the sum total of the carboxylic acids of formula (II), and any Broensted acids that may be present, is in a molar ratio of from 1.01:1 to 2:1 relative to glycidyl (meth)acrylate, and this ratio is present after synthesis and before storage; and
when stored at 30° C. for 8 months, the composition maintains at least 85% by weight diester and no more than 3% by weight triester.