One component (1K) composition based on epoxy resin

Patent metadata

Field	Value
Publication number	US-12338342-B2
Application number	US-202217833072-A
Country	US
Kind code	B2
Filing date	Jun 6, 2022
Priority date	Dec 4, 2019
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

The present invention is directed to an one-component (1K) composition comprising, based on the weight of the composition:
from 30 to 90 wt. % of a) at least one epoxy resin; from 1 to 50 wt. % of b) at least one mercapto compound having at least two mercapto groups reactive towards epoxide; from 0.5 to 25 wt. % of c) at least one organoboron compound selected from tetrasubstituted borate salts of monovalent cations of tertiary amines; and, from 0.5 to 25 wt. % of d) at least one (meth)acrylamide monomer of Formula (VII):

wherein: R a is H or Me;
G is selected from —NH 2 , —NHR b and —N(R b )(R c ); R b and R c are independently selected from C 1 -C 18 alkyl, C 1 -C 18 hydroxyalkyl, C 1 -C 18 alkalkoxy, C 6 -C 18 aryl and —(CH 2 ) n —N(R d )(R e ); n is an integer of from 1 to 4; and, R d and R e are independently selected from H and C 1 -C 6 alkyl.

First claim

What is claimed is:

1. A curable composition comprising, based on the total weight of the composition:
a) at least one epoxy resin present in an amount of from 40 to 60 wt %;
b) at least one mercapto compound having at least two mercapto groups reactive towards epoxide present in an amount of from 10 to 40 wt %;
c) at least one organoboron compound selected from tetrasubstituted borate salts of monovalent cations of tertiary amines present in an amount of from 5 to 20 wt %; and
d) at least one (meth)acrylamide monomer present in an amount of from 5 to 20 wt % and having Formula (VII):

wherein: R a is H or Me;
G is selected from the group consisting of —NH 2 , —NHR b , and —N(R b )(R c );
R b and R c are independently selected from the group consisting of C 1 -C 18 alkyl,
C 1 -C 18 hydroxyalkyl, C 1 -C 18 alkalkoxy, C 6 -C 18 aryl, and —(CH 2 ) n —N(R d )(R e );
n is an integer of from 1 to 4; and
R d and R e are independently selected from the group consisting of H and C 1 -C 6 alkyl,

wherein the composition has a curing temperature of from 50° C. to 200° C.

2. The composition of claim 1 , wherein the molar ratio of epoxy-reactive groups to epoxy groups is from 0.05:1 to 0.95:1.

3. The composition of claim 1 , wherein the at least one epoxy resin is selected from the group consisting of glycidyl ethers of polyhydric alcohols, glycidyl ethers of polyhydric phenols, glycidyl esters of polycarboxylic acids, epoxidized polyethylenically unsaturated hydrocarbons, epoxidized polyethylenically unsaturated esters, epoxidized polyethylenically unsaturated ethers and epoxidized polyethylenically unsaturated amides.

4. The composition of claim 1 , wherein the at least one mercapto compound comprises at least one polyester of a thiocarboxylic acid.

5. The composition of claim 1 , wherein the at least one mercapto compound comprises at least one mercapto compound selected from the group consisting of pentaerythritol tetramercapto-acetate (PETMP), trimethylolpropane trimercaptoacetate (TMPMP), and glycol dimercaptoacetate.

6. The composition of claim 1 , wherein the at least one organoboron compound comprises a cycloamidinium tetrasubstituted borate salt and/or an imidazolium tetrasubstituted borate salt.

7. The composition of claim 1 , wherein the at least one organoboron compound comprises a compound represented by general Formula (III) below:

wherein: R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, C 1 -C 18 alkyl, C 6 -C 18 aryl, C 3 -C 18 cycloalkyl, C 2 -C 20 alkenyl, —C(O) R q , —C(O)OH, —CN, and —NO 2 ;
R q is C 1 -C 6 alkyl; and
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 18 aryl, and C 7 -C 24 alkylaryl.

8. The composition of claim 7 , wherein R 6 , R 7 , R 8 and R 9 are all the same and are selected from the group consisting of C 1 -C 6 alkyl and phenyl.

9. The composition of claim 7 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 6 -C 18 aryl, C 3 -C 12 cycloalkyl, C 2 -C 6 alkenyl, —CO 2 H, —CN, and —NO 2 .

10. The composition of claim 1 , wherein the at least one organoboron compound comprises a compound represented by general Formula (VI) below:

wherein: R 10 is selected from the group consisting of H, C 1 -C 6 alkyl, C 6 -C 18 aryl, C 7 -C 24 aralkyl, C 3 -C 18 cycloalkyl, and C 2 -C 20 alkenyl;
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 18 aryl and C 7 -C 24 alkylaryl; and
n is an integer of from 1 to 3.

11. The composition of claim 10 , wherein R 10 is selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, phenyl, naphthyl, benzyl, and tolyl.

12. The composition of claim 1 , wherein the at least one organoboron compound comprises at least one salt selected from the group consisting of imidazolium tetraphenylborate, methylimidazolium tetraphenylborate, 2-ethyl-4-methylimidazolium tetraphenylborate, 2-ethyl-1,4-dimethylimidazolium tetraphenylborate, 8-benzyl-1,8-diazabicyclo[5.4.0]undec-7-enium tetraphenylborate, 1,8-diazabicyclo[5.4.0]undec-7-ene tetraphenylborate, and 1,5-diazabicyclo[4.3.0]-non-5-ene tetraphenylborate.

13. The composition of claim 1 , wherein the at least one (meth)acrylamide monomer has Formula (VII):

wherein: R a is H or Me;
G is selected from the group consisting of —NH 2 , —NHR b and —N(R b )(R c );
R b and R c are independently selected from the group consisting of C 1 -C 12 alkyl,
C 1 -C 12 hydroxyalkyl, C 1 -C 12 alkalkoxy and —(CH 2 ) n —NR d R e ;
n is an integer of from 2 to 4; and
R d and R e are C 1 -C 4 alkyl.

14. The composition of claim 1 , wherein the at least one (meth)acrylamide monomer is selected from the group consisting of (meth)acrylamide, N-methyl (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-n-butyl (meth)acrylamide, N-t-butyl (meth)acrylamide, N,N-di-n-butyl (meth)acrylamide, N-octyl (meth)acrylamide, N-dodecyl (meth)acrylamide, N-octadecyl (meth)acrylamide, N-phenyl (meth)acrylamide, N,N-dimethylaminoethyl (meth)acrylamide, N-(2-methoxyethyl) (meth)acrylamide, N-(2-ethoxyethyl) (meth)acrylamide, N-(2-hydroxyethyl) (meth)acrylamide, and N-(2-hydroxylpropyl) (meth)acrylamide.

15. The composition of claim 1 , further comprising at least one epoxy silane coupling agent present in an amount up to about 5 wt %, based on the total weight of the composition.

16. The composition of claim 1 , further comprising a plasticizer present in an amount of up to about 10 wt %, based on the total weight of the composition.

17. The composition of claim 1 , wherein the composition has a curing temperature of from 50° C. to 150° C.

18. The composition of claim 17 , wherein the composition has a curing temperature of from 70° C. to 120° C.

19. A product obtained from curing the composition of claim 1 .

20. A curable composition comprising, based on the weight of the composition:
a) bisphenol A liquid epoxy resin present in an amount of from 40 to 60 wt %;
b) pentaerythritol tetrakis(3-mercaptopropionate) present in an amount of from 10 to 40 wt %;
c) 2-ethyl-4-methylimidazolium tetraphenyl borate present in an amount of from 5 to 20 wt %; and
d) N,N-dimethyl acrylamide present in an amount of from 5 to 20 wt %.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Chen Chunfu

Classifications

• C08K5/37

  Thiols · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title

• C08K5/55 Primary

  Boron-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• C08G59/24

  carbocyclic · CPC title