Dual cure polythioether

Patent metadata

Field	Value
Publication number	US-2020308403-A1
Application number	US-202016946253-A
Country	US
Kind code	A1
Filing date	Jun 12, 2020
Priority date	Dec 23, 2014
Publication date	Oct 1, 2020
Grant date	—

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

• C08K3/26

  Carbonates; Bicarbonates · CPC title

• C08G75/02 Primary

  Polythioethers · CPC title

• C08L81/02 Primary

  Polythioethers; Polythioether-ethers · CPC title

• C08G75/00

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title

• C08G18/04

  with vinyl compounds · CPC title