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US 11,236,201 B2Granted
Sulfur-containing poly(alkenyl) ethers, prepolymers incorporating sulfur-containing poly(alkenyl) ethers, and uses thereof
AssigneePRC-DeSoto International, Inc.
InventorsWeibin Cui, Renhe Lin
Life of this patent
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Abstract
Sulfur-containing poly(alkenyl) ethers can be incorporated into the backbone of polythioether prepolymers and can be used as curing agents in thiol-terminated polythioether prepolymer compositions. Cured sealants prepared using compositions containing sulfur-containing poly(alkenyl) ether-containing polythioether prepolymers and/or sulfur-containing poly(alkenyl) ether curing agents exhibit improved physical properties suitable for use in aerospace sealant applications.
Claims21
A polythioether prepolymer comprising a moiety of Formula (2):
- —S—R1—[S-A-S—R1—]s—S— (2)
- wherein,
- s is an integer from 1 to 60;
- each R1 is independently selected from C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, and —[(—CHR—)p—X—]q—(CHR)r—, wherein each R is independently selected from hydrogen and methyl, wherein,
- each X is independently selected from —O— and —S—;
- each p is independently an integer from 2 to 6;
- q is an integer from 1 to 5;
- and
- r is an integer from 2 to 10;
- each A is independently selected from a sulfur-containing moiety of Formula (3a), a moiety of Formula (4a), and a moiety derived from an alkenyl-terminated polyfunctionalizing agent, wherein from 10 mol % to 90 mol % of the A moieties comprise a sulfur-containing moiety of Formula (3a):
- —(CH2)2—O—(CH2)n—Y1—R4—Y1—(CH2)n—O—(CH2)2— (3a)
- —(CH2)2—O—(R2—O)m—(CH2)2— (4a)
- wherein,
- each n is independently an integer from 1 to 4;
- each Y1 is independently selected from —O— and —S—;
- m is an integer from 0 to 50;
- and
- each R2 is independently selected from C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, and
- —[(CH2)p—X—]q—(CH2)r—, wherein,
- each p is independently an integer from 2 to 6;
- q is an integer from 1 to 5;
- and
- r is an integer from 2 to 10;
- R4 is selected from C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, and —[(CH2)p—X—]q—(CH2)r—, wherein,
- each X is independently selected from —O—, —S—, and —S—S—;
- each p is an integer from 2 to 6;
- q is an integer from 1 to 5;
- and
- r is an integer from 2 to 10;
- and
- at least one Y1 is —S—, or R4 is —[(CH2)p—X—]q—(CH2)r— and at least one X is selected from —S— and —S—S—,
- wherein mol % is based on the total moles of A moieties in the prepolymer.
29 more elements
A polythioether prepolymer comprising reaction products of reactants comprising:
- (a) a polythiol comprising a dithiol of Formula (7):
- HS—R1—SH (7)
- wherein,
- R1 is selected from C2-10 alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, C5-8 heterocycloalkanediyl, and
- —[—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— and —S—;
- and
- (b) a sulfur-containing bis(alkenyl) ether of Formula (3):
- CH2═CH—O—(CH2)n—Y1—R4—Y1—(CH2)n—O—CH═CH2 (3)
- wherein,
- each n is independently an integer from 1 to 4;
- each Y1 is independently selected from —O— and —S—;
- and
- R4 is selected from C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, and —[(CH2)p—X—]q—(CH2)r—,
- wherein,
- each X is independently selected from —O—, —S—, and —S—S—;
- 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;
- and
- at least one Y1 is —S—, or R4 is —[(CH2)p—X—]q—(CH2)r— and at least one X is selected from —S— and —S—S—;
- and
- (c) a divinyl ether of Formula (4):
- CH2═CH—O—(—R2—O—)m—CH═CH2 (4)
- wherein,
- m is an integer from 0 to 50;
- and
- each R2 is independently selected from C2-6 n-alkanediyl, C3-6 branched alkanediyl, C6-8 cycloalkanediyl, C6-10 alkanecycloalkanediyl, and
- —[(CH2)p—X—]q—(CH2)r—, wherein,
- each p is independently an integer from 2 to 6;
- q is an integer from 1 to 5;
- and
- r is an integer from 2 to 10;
- wherein the reactants comprise from 10 mol % to 90 mol % of the sulfur-containing bis(alkenyl) ether of Formula (3), wherein mol % is based on the total moles of the sulfur-containing bis(alkenyl) ether of Formula (3) and the divinyl ether of Formula (4).
36 more elements
Dependencies are inferred from the claim text.