Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof

A polythioether prepolymer comprising a moiety of Formula (1):

• —S—R1—[—S-A-S—R1—]s—S— (1)
• wherein,
• s is an integer from 1 to 60;
• each R1 comprises C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, or —[(—CHR—)p—X—]q—(—CHR—)r—, wherein:
• each p is independently an integer from 2 to 6;
• q is an integer from 1 to 5;
• r is an integer from 2 to 10;
• each R is independently selected from hydrogen and methyl;
• and
• each X is independently selected from —O—, —S—, and —NR5—, wherein R5 is selected from hydrogen and methyl;
• each A independently comprises a moiety of Formula (2a) or a moiety of Formula (3a):
• —(CH2)2—O—R5—Y′—C(═O)—NH—R4—NH—C(═O)—Y′—R5—O—(CH2)2— (2a)
• —(CH2)2—O—(R2—O)m—(CH2)2— (3a)
• wherein,
• m is an integer from 1 to 50;
• each Y′ is independently selected from —O— and —NH—;
• each R2 comprises C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, or —[(—CH2—)p—O—]q—(—CH2—)r—, wherein,
• each p is independently an integer ranging from 2 to 6;
• q is an integer from 1 to 5;
• and
• r is an integer from 2 to 10;
• R4 comprises a core of a diisocyanate;
• each R5 independently comprises C1-10 alkanediyl, C5-10 cycloalkanediyl, or C6-20 cycloalkane-alkanediyl;
• and
• at least one A comprises a moiety of Formula (2a).

A polythioether prepolymer comprising reaction products of reactants comprising:

• (a) a polythiol comprising a dithiol of Formula (6):
• HS—R1—SH (6)
• wherein,
• R1 comprises C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, or —[(—CHR—)p—X—]q—(—CHR—)r—, wherein:
• each p is independently an integer from 2 to 6;
• q is an integer from 1 to 5;
• r is an integer from 2 to 10;
• each R 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;
• (b) a urethane/urea-containing bis(alkenyl) ether of Formula (2):
• CH2═CH—O—R5—Y′—C(═O)—NH—R4—NH—C(═O)—Y′—R5—O—CH═CH2 (2)
• wherein,
• each Y′ independently comprises —NH— or —O—;
• R4 comprises a core of a diisocyanate;
• and
• each R5 independently comprises C1-10 alkanediyl, C5-10 cycloalkanediyl, or C6-20 cycloalkane-alkanediyl;
• and
• (c) a divinyl ether of Formula (3):
• CH2═CH—O—(—R2—O—)m—CH═CH2 (3)
• wherein,
• m is an integer from 0 to 50;
• and
• each R2 independently comprises C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, or —[(—CH2—)p—O—]q—(—CH2—)r—, wherein,
• each p is independently an integer ranging from 2 to 6;
• q is an integer from 1 to 5;
• and
• r is an integer from 2 to 10.