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Compositions comprising sulfur-containing polymers such as polythioethers, Michael acceptors, and controlled release amine catalysts employing Michael addition curing chemistries useful in aerospace sealant applications are disclosed. The compositions exhibit extended pot life and the rate of curing

Compositions comprising sulfur-containing polymers such as polythioethers, Michael acceptors, and controlled release amine catalysts employing Michael addition curing chemistries useful in aerospace sealant applications are disclosed. The compositions exhibit extended pot life and the rate of curing can be tailored for specific applications.

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1. A composition comprising: (a) a compound comprising at least two terminal groups reactive with Michael acceptor groups;(b) a compound having at least two Michael acceptor groups; and(c) a controlled release amine catalyst; wherein,the compound having at least two Michael acceptor groups comprises

1. A composition comprising: (a) a compound comprising at least two terminal groups reactive with Michael acceptor groups;(b) a compound having at least two Michael acceptor groups; and(c) a controlled release amine catalyst; wherein,the compound having at least two Michael acceptor groups comprises a polythioether adduct selected from a polythioether adduct of Formula (3), a polythioether adduct of Formula (3a), and a combination thereof: R6—S—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—S—R6  (3){R6—S—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—S—V′—}zB  (3a)wherein: each R1 independently is selected from C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)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 R3 is independently selected from hydrogen and methyl; andeach X is independently selected from —O—, —S—, and —NR—,wherein R is selected from hydrogen and methyl;each R2 is independently selected from C1-10 alkanediyl, C6-8 cycloalkanediyl, C6-14 alkanecycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)r—, wherein s, q, r, R3, and X are as defined for R1;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; andeach V is a group comprising a terminal vinyl group; andeach —V′— is derived from the reaction of —V with a thiol; andeach R6 is independently a moiety comprising a terminal Michael acceptor group selected from a vinyl ketone, a quinone, an enamine, a ketamine, an aldimine, and an oxazolidine. 2. The composition of claim 1, wherein the compound (a) has a molecular weight less than 400 Daltons. 3. The composition of claim 1, wherein the compound (a) comprises a polythioether polymer selected from a polythioether polymer of Formula (4), a polythioether polymer of Formula (4a), and a combination thereof: HS—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—SH  (4){HS—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—S—V′—}zB  (4a)wherein: each R1 independently is selected from C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-14 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)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 R3 is independently selected from hydrogen and methyl; andeach X is independently selected from —O—, —S—, and —NR—,wherein R is selected from hydrogen and methyl;each R2 is independently selected from C1-10 alkanediyl, C6-8 cycloalkanediyl, C6-14 alkanecycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)r—, wherein s, q, r, R3, and X are as defined as for R1;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; andeach V is a group comprising a terminal vinyl group; andeach —V′— is derived from the reaction of —V with a thiol. 4. The composition of claim 1, wherein the compound having at least two Michael acceptor groups has a molecular weight less than 400 Daltons. 5. The composition of claim 1, wherein the polythioether adduct comprises the reaction products of reactants comprising: (a) a polythioether polymer; and(b) a compound having a Michael acceptor group selected from a vinyl ketone, a quinone, an enamine, a ketamine, an aldimine, and an oxazolidine; and a group that is reactive with a terminal group of the polythioether polymer. 6. The composition of claim 5, wherein the polythioether polymer comprises a polythioether polymer selected from a polythioether polymer of Formula (4), a polythioether polymer of Formula (4a), and a combination thereof: HS—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—SH  (4){HS—R1—[—S—(CH2)p—O—(R2—O)m—(CH2)2—S—R1—]n—S—V′—}zB  (4a)wherein: each R1 independently is selected from C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-14 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)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 R3 is independently selected from hydrogen and methyl; andeach X is independently selected from —O—, —S—, and —NR—,wherein R is selected from hydrogen and methyl;each R2 is independently selected from C1-10 alkanediyl, C6-8 cycloalkanediyl, C6-14 alkanecycloalkanediyl, and —[(—CHR3—)s—X—]q—(—CHR3—)r—, wherein s, q, r, R3, and X are as defined for R1;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; andeach —V is a group comprising a terminal vinyl group; andeach —V′— is derived from the reaction of —V with a thiol. 7. The composition of claim 1, comprising a polyepoxy. 8. The composition of claim 1, comprising a monomeric compound having at least two Michael acceptor groups. 9. The composition of claim 1, wherein the amine catalyst is selected from 1,8-diazabicycloundec-7-ene (DBU), 1,4-diazabicyclo [2.2.2]octane (DABCO), isophorone diamine (IPDA), and a C6-10 primary amine, and a combination of any of the foregoing. 10. The composition of claim 1, wherein the controlled release amine catalyst comprises a blocked amine catalyst. 11. The composition of claim 10, wherein the blocked amine catalyst is capable of being unblocked by exposure to ultraviolet radiation to release a catalytic amine catalyst. 12. The composition of claim 10, wherein the blocked amine catalyst is capable of being unblocked in the presence of moisture to release a catalytic amine catalyst. 13. The composition of claim 1, wherein the controlled release amine catalyst comprises a matrix encapsulant comprising an amine catalyst. 14. The composition of claim 13, wherein the matrix encapsulant is capable of releasing the amine catalyst upon heating or ultrasonication. 15. The composition of claim 1, formulated as a sealant. 16. A sealed surface comprising a cured composition of claim 15. 17. A method of sealing a surface, comprising: applying the composition of claim 15 to a surface; andcuring the composition to provide a sealed surface.