Hexahydrotriazine, dithiazine, and thioether functionalized materials

Patent metadata

Field	Value
Publication number	US-9422378-B2
Application number	US-201414510477-A
Country	US
Kind code	B2
Filing date	Oct 9, 2014
Priority date	Oct 9, 2014
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

Synthetic schemes for preparation of polymers and polymer precursors having various functional groups is provided. These synthetic schemes are used to prepare polymeric, oligomeric, or monomeric materials incorporating 1,3,5-hexahydrotriazine moieties. These hexandortriazine moieties can be further reacted to form dithiazine and thioether moieties. In certain synthetic schemes, 1,3,5-hexahydrotriazine moieties are incorporated as crosslinker groups for providing crosslinked polymeric materials. Crosslinker groups formed with these triazine moieties provide chemically reversible crosslinks, which allow such otherwise intractable crosslinked polymeric materials to be recycled and/or reprocessed by removal/reversal of crosslinks.

First claim

What is claimed is:

1. A polymer, comprising:
a first polymeric repeat unit with a first pendant group having a structure selected from:

wherein each R group includes at least one carbon atom and each starred (*) bond represents a point of attachment to the first polymeric repeat unit.

2. The polymer of claim 1 having the formula:

where n represents a number of first polymeric repeat units in the polymer.

3. The polymer of claim 1 , wherein the polymer is one of a substituted polystyrene, a polymethacrylate, a polycarbonate, and a poly(aryl ether).

4. The polymer of claim 1 , wherein the first polymeric repeat unit has a backbone group including at least one of a styrene group, a methacrylate group, a bisphenol group, a phenylene group, or an ether linkage.

5. A polymer, comprising:
a first polymeric repeat unit selected from:

and
a first pendant group having a structure selected from:

wherein
each starred (*) bond represents a point of attachment between the first polymeric repeat unit and the first pendant group, and
each R group includes at least one carbon atom.

6. The polymer of claim 5 , wherein the first pendant group is one of

and
each R group on the first pendant group is different from the other R group on the first pendant group.

7. The polymer of claim 5 , wherein the first pendant group is one of

and
each R group on the first pendant group is the same as the other R group on the first pendant group.

8. The polymer of claim 5 , wherein the first pendant group is one of

and
wherein each R group on the first pendant group is an alkyl group.

9. The polymer of claim 5 , wherein the first pendant group is one of

and
each R group on the first pendant group includes at least one group selected from an aryl group, a silane group, an alkyne group, an alkene group, an alcohol group, an epoxide group, an amine group, a cyanate group, a carboxylic group, an ester group, a phenolic group, and a succinimide group.

10. The polymer of claim 5 , wherein the first pendant group is one of

and
at least one R group on the first pendant group is a crosslinking group linked to a pendant group on another first polymeric repeat unit.

11. The polymer of claim 5 , wherein the first polymeric repeat unit is

12. The polymer of claim 5 , wherein the first polymeric repeat unit is

13. The polymer of claim 5 , wherein the first polymeric repeat unit is

14. The polymer of claim 5 , wherein the first pendant group is

15. The polymer of claim 5 , wherein the first pendant group is

16. The polymer of claim 5 , wherein the first pendant group is

17. A polymer, comprising:

wherein
n represents a number of repeat units, and
each R group includes at least one carbon atom.

18. The polymer of claim 17 , wherein each R group on a repeat unit is different from the other R group on the repeat unit.

19. The polymer of claim 17 , wherein each R group is an alkyl group.

20. The polymer of claim 17 , wherein each R group includes at least one group selected from an aryl group, a silane group, an alkyne group, an alkene group, an alcohol group, an epoxide group, an amine group, a cyanate group, a carboxylic group, an ester group, a phenolic group, and a succinimide group.

Assignees

• IBM

Inventors

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

Classifications

• C08F8/34

  Introducing sulfur atoms or sulfur-containing groups · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C08G75/23

  Polyethersulfones · CPC title

• C08G65/00

  Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule · CPC title

• C08F12/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title