Preparation of thioether polymers

Patent metadata

Field	Value
Publication number	US-9228059-B2
Application number	US-201414571456-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	May 27, 2014
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

Polythioethers and methods for forming polythioethers are disclosed herein. The polythioethers are prepared from thiols and hexahydrotriazines. The thiols may be, for example, dithiols, trithiols, monothiols, or mixtures thereof. The polythioethers are prepared from an efficient and simple synthetic method, and the properties of the prepared polythioethers can be readily tuned. The prepared polythioethers may additionally have improved thermal properties, improved mechanical properties, and enhanced functionality.

First claim

What is claimed is:

1. A method of forming a polythioether having the repeat unit

the method comprising:
reacting a first hexahydrotriazine of the general formula

with a first dithiol having the general formula

wherein each A is independently selected from a substituted or unsubstituted alkane group, a substituted or unsubstituted alkene group, a substituted or unsubstituted alkyne group, a substituted or unsubstituted aromatic group, or a substituted or unsubstituted heterocyclic group, and wherein each B is an alkane group, an aromatic group, an ether group, a thioether group, or a ketone group.

2. The method of claim 1 , wherein B comprises

wherein R is bonded to the 2 or 3 carbon, and wherein R is selected from the group consisting of:

wherein R′ comprises an alkane group, L comprises an alkane group, and wherein * indicates the location on the R where R bonds to the B.

3. The method of claim 2 , wherein A is selected from the group consisting of substituted and unsubstituted alkane groups and substituted and unsubstituted aromatic groups.

4. The method of claim 3 , further comprising reacting the first hexahydrotriazine and first dithiol with a trithiol.

5. The method of claim 3 , further comprising reacting the first hexahydrotriazine and first dithiol with a monothiol.

6. The method of claim 3 , further comprising reacting the hexahydrotriazine and dithiol with a second hexahydrotriazine, wherein the second hexahydrotriazine is distinct from the first hexahydrotriazine.

7. The method of claim 3 , further comprising reacting the hexahydrotriazine and dithiol with a second dithiol, wherein the second dithiol is distinct from the first dithiol.

8. The method of claim 3 , wherein A comprises an N,N-dimethylaniline group.

Assignees

• IBM

Inventors

• Boday Dylan J
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• C08G75/04 Primary

  from mercapto compounds or metallic derivatives thereof (C08G75/0204 takes precedence) · CPC title

• C08G75/0268

  using disulfides · CPC title

• C08G75/025 Primary

  Preparatory processes · 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

• C08G75/0227

  derived from monomers containing two or more aromatic rings · CPC title