Michael addition curing chemistries for sulfur-containing polymer compositions employing bis(sulfonyl)alkanols

1. A sulfur-containing Michael acceptor adduct comprising at least two terminal 1-(ethylenesulfonyl)-n-(vinylsulfonyl)alkanol groups.

2. The adduct of claim 1 , wherein each of the at least two terminal 1-(ethylenesulfonyl)-n-(vinylsulfonyl)alkanol groups are 1-(ethylenesulfonyl)-3-(vinylsulfonyl)propan-2-ol groups.

3. The adduct of claim 1 , wherein the adduct is selected from a polythioether Michael acceptor adduct of Formula (3), a polythioether Michael acceptor adduct of Formula (3a), and a combination thereof:

R 6 —S—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —S—R 6   (3)

{R 6 —S—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —S—V′—} z B  (3a)

wherein:

each R 1 independently is selected from C 2-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-10 alkanecycloalkanediyl, C 5-8 heterocycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 -) r —, wherein:

s is an integer from 2 to 6;

q is an integer from 1 to 5;

r is an integer from 2 to 10;

each R 3 is independently selected from hydrogen and methyl; and

each X is independently selected from —O—, —S—, and —NR—, wherein R is selected from hydrogen and methyl;

each R 2 is independently selected from C 1-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-14 alkanecycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 -) r —, wherein s, q, r, R 3 , and X are as defined for R 1 ;

m is an integer from 0 to 50;

n is an integer from 1 to 60;

p is an integer from 2 to 6;

B represents a core of a z-valent, vinyl-terminated polyfunctionalizing agent B(—V) z wherein:

z is an integer from 3 to 6; and

each V is a group comprising a group reactive with thiol groups; and

each —V′— is derived from the reaction of —V with a thiol; and

each R 6 is independently a moiety comprising a terminal 1-(ethylenesulfonyl)-n-(vinylsulfonyl)alkanol group.

4. The adduct of claim 3 , wherein each R 6 has the structure of Formula (2):

—CH 2 —CH 2 —S(O) 2 —R 15 —CH(—OH)—R 15 —S(O) 2 —CH═CH 2   (2)

wherein each R 15 is independently selected from C 1-3 alkanediyl, and substituted C 1-3 alkanediyl, wherein the one or more substituent groups is —OH.

5. The adduct of claim 1 , wherein the adduct comprises the reaction products of reactants comprising:

(a) a sulfur-containing polymer; and

(b) a compound having a terminal bis(sulfonyl)alkanol group and a group that is reactive with a terminal group of the sulfur-containing polymer.

6. The adduct of claim 5 , wherein the sulfur-containing polymer comprises a thiol-terminated polythioether selected from a thiol-terminated polythioether polymer of Formula (4), a thiol-terminated polythioether polymer of Formula (4a), and a combination thereof:

HS—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —SH  (4)

{HS—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —S—V′—} z B  (4a)

wherein:

each R 1 independently is selected from C 2-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-14 alkanecycloalkanediyl, C 5-8 heterocycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 -) r —, wherein:

s is an integer from 2 to 6;

q is an integer from 1 to 5;

r is an integer from 2 to 10;

each R 3 is independently selected from hydrogen and methyl; and

each X is independently selected from —O—, —S—, and —NR—, wherein R is selected from hydrogen and methyl;

each R 2 is independently selected from C 1-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-14 alkanecycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 -) r —, wherein s, q, r, R 3 , and X are as defined for R 1 ;

m is an integer from 0 to 50;

n is an integer from 1 to 60;

p is an integer from 2 to 6;

B represents a core of a z-valent, vinyl-terminated polyfunctionalizing agent B(—V) z wherein:

z is an integer from 3 to 6; and

each —V is a group comprising a terminal group reactive with thiol groups; and

each —V′— is derived from the reaction of —V with a thiol.

7. The adduct of claim 5 , wherein the compound having a terminal bis(sulfonyl)alkanol group and a group that is reactive with a terminal group of the sulfur-containing polymer comprises 1,3-bis(vinylsulfonyl)-2-propanol.

8. A composition comprising:

(a) a sulfur-containing polymer comprising at least two terminal groups reactive with Michael acceptor groups; and

(b) a bis(vinylsulfonyl)alkanol.

9. The composition of claim 8 , wherein the bis(vinylsulfonyl)alkanol is 1,3-bis(vinylsulfonyl)-2-propanol.

10. The composition of claim 8 , comprising a polyepoxy.

11. The composition of claim 8 , comprising a polysulfide polymer comprising at least two terminal groups reactive with Michael acceptor groups.

12. A composition comprising:

(a) the sulfur-containing Michael acceptor adduct of claim 1 ; and

(b) a curing agent comprising at least two terminal groups that are reactive with Michael acceptor groups.

13. The composition of claim 12 , wherein the curing agent is selected from a sulfur-containing polymer comprising at least two terminal groups reactive with Michael acceptor groups, a monomeric thiol, a polythiol, a polyamine, a blocked amine, and a combination of any of the foregoing.

14. The composition of claim 12 , wherein the curing agent comprises a sulfur-containing polymer comprising at least two terminal groups reactive with Michael acceptor groups.

15. The composition of claim 14 , wherein the sulfur-containing polymer comprises a polythioether.

16. The composition of claim 15 , wherein the polythioether comprises a thiol-terminated polythioether selected from a thiol-terminated polythioether polymer of Formula (4), a thiol-terminated polythioether polymer of Formula (4a), and a combination thereof:

HS—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —SH  (4)

{HS—R 1 -[—S—(CH 2 ) p —O—(R 2 —O) m —(CH 2 ) 2 —S—R 1 -] n —S—V′—} z B  (4a)

wherein:

each R 1 independently is selected from C 2-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-14 alkanecycloalkanediyl, C 5-8 heterocycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 -) r —, wherein:

s is an integer from 2 to 6;

q is an integer from 1 to 5;

r is an integer from 2 to 10;

each R 3 is independently selected from hydrogen and methyl; and

each X is independently selected from —O—, —S—, and —NR—, wherein R is selected from hydrogen and methyl;

each R 2 is independently selected from C 1-10 alkanediyl, C 6-8 cycloalkanediyl, C 6-14 alkanecycloalkanediyl, and -[(—CHR 3 -) s —X-] q -(—CHR 3 —) r —, wherein s, q, r, R 3 , and X are as defined as for R 1 ;

m is an integer from 0 to 50;

n is an integer from 1 to 60;

p is an integer from 2 to 6;

B represents a core of a z-valent, vinyl-terminated polyfunctionalizing agent B(—V) z wherein:

z is an integer from 3 to 6; and

each V is a group comprising a terminal group reactive with thiol groups; and

each —V′— is derived from the reaction of —V with a thiol.

17. The composition of claim 14 , wherein the sulfur-containing polymer comprises a polysulfide polymer.

18. The composition of claim 12 , comprising a polyepoxy.

19. The composition of claim 12 , comprising a polysulfide Michael acceptor adduct.

20. A composition comprising:

(a) a sulfur-containing Michael acceptor adduct of claim 1 ;

(b) a sulfur-containing polymer comprising at least two terminal groups reactive with Michael acceptor groups; and

(c) a monomeric compound having at least two Michael acceptor groups.

21. The composition of claim 12 , formulated as a sealant.

22. A cured sealant prepared using the composition of claim 21 .

23. A method of sealing a surface comprising:

providing a surface;

applying the composition of claim 21 to the surface; and

curing the composition to provide a sealed surface.

24. The composition of claim 20 , formulated as a sealant.

25. A cured sealant prepared using the composition of claim 24 .

26. A method of sealing a surface comprising:

providing a surface;

applying the composition of claim 24 to the surface; and

curing the composition to provide a sealed surface.