Dual cure polythioether

Patent metadata

Field	Value
Publication number	US-11319440-B2
Application number	US-202016946253-A
Country	US
Kind code	B2
Filing date	Jun 12, 2020
Priority date	Dec 23, 2014
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

Compositions that are curable to polythioether polymers are provided, comprising: a) a dithiol monomer; b) a diene monomer; c) a radical cleaved photoinitiator; d) a peroxide; and e) an amine; where the peroxide and amine together are a peroxide-amine redox initiator. In some embodiments, the amine is a tertiary amine. In some embodiments, the amine is selected from the group consisting of dihydroxyethyl-p-toluidine, N,N-diisopropylethylamine, and N, N, N′, N″, N″-pentamethyl-diethylenetriamine. In some embodiments, the peroxide is selected from the group consisting of di-tert-butyl peroxide, methyl ethyl ketone peroxide, and benzoyl peroxide. In some embodiments, the composition may additionally comprise a polythiol monomer having three or more thiol groups.

First claim

We claim:

1. A two-part composition that is curable to a polythioether polymer, comprising the following the components in a Part A and/or a part B:
a) products from the reaction of at least one of each of: dithiol monomers, dienes, trienes, and epoxy resins;
b) a diene monomer;
c) a radical cleaved photoinitiator;
d) a peroxide; and
e) an amine;

wherein the peroxide and the amine are in different part from each other, and where the peroxide and amine together are a peroxide-amine redox initiator, wherein a polyether resulting from curing the composition has a glass transition temperature of lower than −40° C.

2. The composition according to claim 1 where the amine is a tertiary amine.

3. The composition according to claim 1 , wherein component (a) further comprises a tertiary amine catalyst and a thermal free radical initiator.

4. The composition according to claim 1 where the amine is selected from the group consisting of dihydroxyethyl-p-toluidine, N,N-diisopropylethylamine, and N, N, N′, N″, N″-pentamethyl-diethylenetriamine.

5. The composition according to claim 1 where the peroxide is selected from the group consisting of di-tert-butyl peroxide, methyl ethyl ketone peroxide, and benzoyl peroxide.

6. The composition according to claim 1 additionally comprising:
f) a polythiol monomer having three or more thiol groups.

7. The composition according to claim 1 additionally comprising:
g) at least one filler.

8. The composition according to claim 1 additionally comprising:
h) at least one nanoparticle filler.

9. The composition according to claim 1 additionally comprising:
j) calcium carbonate.

10. The composition according to claim 1 additionally comprising:
k) nanoparticle calcium carbonate.

11. The composition according to claim 1 which is curable by actinic light source.

12. The composition according to claim 1 which is curable by blue light source.

13. The composition according to claim 1 which is curable by UV light source.

14. A sealant comprising the composition according to claim 1 .

15. A polythioether polymer obtained by cure of the composition according to claim 1 .

16. The composition according to claim 4 , where the peroxide is selected from the group consisting of di-tert-butyl peroxide, methyl ethyl ketone peroxide, and benzoyl peroxide.

17. The composition according to claim 3 additionally comprising:
k) nanoparticle calcium carbonate.

18. The composition according to claim 16 additionally comprising:
k) nanoparticle calcium carbonate.

Assignees

• 3M Innovative Properties Co

Inventors

• Ye Sheng
• Li Junting
• Wang Yizhong
• Oxman Joel D
• Demoss Susan E
• Zook Jonathan D

Classifications

• C09J181/02

  Polythioethers; Polythioether-ethers · CPC title

• B64D45/02

  Lightning protectors; Static dischargers · CPC title

• C08K2201/011

  Nanostructured additives · CPC title

• C08K3/26

  Carbonates; Bicarbonates · CPC title

• C08L81/02 Primary

  Polythioethers; Polythioether-ethers · CPC title