Dual cure sealants

Patent metadata

Field	Value
Publication number	US-12559593-B2
Application number	US-202318295833-A
Country	US
Kind code	B2
Filing date	Apr 4, 2023
Priority date	Jun 9, 2017
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

Compositions that are curable by free radical redox reactions are disclosed. Free radical curing reactions between polythiols and polyalkyenyls are initiated by the reaction of metal complexes and organic peroxides. The compositions are useful as sealants.

First claim

What is claimed is:

1 . A composition comprising:
a polythiol, wherein the polythiol comprises a thiol-terminated polythioether prepolymer; a bis(alkenyl) ether monomer; a hydroxyl-functional vinyl ether monomer; a hydrogen donor; from 0.001 wt % to 3 wt % of a metal complex; and from 0.01 wt % to 4 wt % of an organic peroxide; wherein wt % is based on the total weight of the composition.

2 . The composition of claim 1 , wherein the polythiol further comprises a polythiol monomer.

3 . The composition of claim 1 , wherein the bis(alkenyl) ether monomer comprises cyclohexanedimethanol divinyl ether, tetraethyleneglycol divinyl ether, or a combination thereof.

4 . The composition of claim 1 , wherein the metal complex comprises a metal complex of Co(II), Co(III), Mn(II), Mn(III), Fe(II), Fe(III), Cu(II), V(III), or a combination of any of the foregoing.

5 . The composition of claim 1 , wherein the metal complex comprises cobalt(II)bis(2-ethyl hexanoate), manganese(III)(acetylacetonate) 3 , iron(III)(acetylacetonate) 3 , or a combination of any of the foregoing.

6 . The composition of claim 1 , wherein the organic peroxide comprises tert-butyl peroxybenzoate.

7 . The composition of claim 1 , wherein the composition comprises a free radical photoinitiator.

8 . The composition of claim 1 , wherein the hydrogen donor comprises a primary amine, a secondary amine or a combination thereof.

9 . The composition of claim 1 , wherein,
the composition comprises from 0.01 wt % to 2 wt % of the hydrogen donor; and wt % is based on the total weight of the composition.

10 . The composition of claim 1 , wherein the composition is curable under dark conditions.

11 . The composition of claim 1 , wherein the composition is curable upon exposure to actinic radiation.

12 . The composition of claim 1 , wherein the composition is curable without exposure to actinic radiation.

13 . The composition of claim 1 , wherein the composition is curable at a temperature from 20° C. to 30° C.

14 . A cured sealant prepared from the composition of claim 1 .

15 . A part sealed with the cured sealant of claim 14 .

16 . A vehicle comprising the cured sealant of claim 14 .

17 . An aerospace vehicle comprising the cured sealant of claim 14 .

18 . A method of sealing a part comprising:
applying the composition of claim 1 to a part; and allowing the applied composition to cure, to seal the part.

19 . The composition of claim 1 , wherein the hydroxyl-functional vinyl ether monomer comprises 4-hydroxybutyl vinyl ether.

20 . The composition of claim 1 , wherein the composition comprises:
from 55 wt % to 75 wt % of the thiol-terminated polythioether prepolymer; from 2 wt % to 10 wt % of the bis(alkenyl) ether monomer; from 0.1 wt % to 2 wt % the hydroxyl-functional vinyl ether monomer; from 0.01 wt % to 2 wt % of the hydrogen donor; from 0.01 wt % to 3 wt % of the metal complex; and from 0.2 wt % to 3 wt % of the organic peroxide.

21 . The composition of claim 20 , wherein the composition comprises from 0.01 wt % to 2 wt % of an actinic radiation free radical polymerization initiator.

22 . The composition of claim 1 , wherein
the bis(alkenyl) ether monomer comprises cyclohexanedimethanol divinyl ether, tetraethyleneglycol divinyl ether, or a combination thereof; the hydroxyl-functional vinyl ether monomer comprises 4-hydroxybutyl vinyl ether; the hydrogen donor comprises a primary amine, a secondary amine, or a combination thereof; the metal complex comprises cobalt(II) bis(2-ethyl hexanoate), manganese(III)(acetylacetonate) 3 , iron(III)(acetylacetonate) 3 , or a combination of any of the foregoing; and the organic peroxide comprises tert-butyl peroxybenzoate.

Assignees

• Prc Desoto Int Inc

Inventors

• Liu Jiancheng
• Pathak Srikant
• Virnelson Bruce

Classifications

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08K5/14

  Peroxides · CPC title

• C08K5/0091

  Complexes with metal-heteroatom-bonds · CPC title

• C08J7/18

  using wave energy or particle radiation · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title