Granted Patent B2

US 12,410,118 · App. 17/750,383 · Granted Sep 9, 2025

Inventors: Patrik Hartmann (Buettelborn, DE); Marita Kaufmann (Griesheim, DE); Steffen Krill (Mühltal, DE); Thorben Schütz (Alsbach-Hähnlein, DE); Marcel Treskow (Darmstadt, DE); Andrea Wittkowski (Gross-Umstadt, DE)

Assignee: Evonik Operations GmbH

C07C69/732

Abstract

Claims (26)

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:

and wherein:

R 1 is selected from the group consisting of H and CH3;

R 2 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):

wherein R 2 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.

2. The storage stable composition of claim 1 , wherein, the sum total of the carboxylic acids of formula (II) and Broensted acids are present in a molar ratio of from 1.02:1 to 1.5:1, relative to glycidyl (meth)acrylate and when stored at 50° C., storage stability lasts more than 6 months.

3. The storage stable composition of claim 1 , wherein Broensted acids are not present.

4. The storage stable composition of claim 1 , wherein Broensted acids are present.

5. The storage stable composition of claim 1 , wherein the glycerol (meth)acrylate carboxylic esters are present as a mixture of esters of Formula (I) A and Formula (I) B.

6. The storage stable composition of claim 1 , wherein R1 is methyl.

7. The storage stable composition of claim 1 , wherein R2 is a C1 to C30 aliphatic group optionally with a hydroxyl substituent or a C2 to C30 unsaturated aliphatic group.

8. The storage stable composition of claim 1 , wherein R2 is a C2 to C30 unsaturated aliphatic group.

9. The storage stable composition of claim 1 , wherein R2 is 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; or a C2 to C30 unsaturated aliphatic group.

10. The storage stable composition of claim 1 , wherein R2 is 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.

11. The storage stable composition of claim 10 , wherein R1 is methyl.

12. The storage stable composition of claim 11 , wherein Broensted acids are not present.

13. The storage stable composition of claim 12 , wherein Broensted acids are present.

14. The storage stable composition of claim 1 , wherein R2 is isobutene.

15. The storage stable composition of claim 14 , wherein R1 is methyl.

16. The storage stable composition of claim 15 , wherein Broensted acids are not present.

Assignments (5)

Priority Claims (1)

Continuity (2)

References Cited (71)