High molecular weight polythioaminals from a single monomer

Patent metadata

Field	Value
Publication number	US-9534084-B1
Application number	US-201514930435-A
Country	US
Kind code	B1
Filing date	Nov 2, 2015
Priority date	Nov 2, 2015
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

Compounds include polythioaminals of the formula:

Each instance of R may be hydrogen or an electron withdrawing group. ‘n’ may be an integer such that the number average molecular weight (Mn) or weight average molecular weight (Mw) is between about 2,000 to about 80,000. Compounds also include polythioaminals of the formula:

Each instance of R may be independently selected from the group consisting of —H, —F, —CF 3 , and —NO 2 . Each instance of R′ may be independently selected from the group consisting of cycloalkyl, alkyl, alkylene glycol, acrylate, and siloxane. ‘n’ may be an integer such that the number average molecular weight (Mn) or weight average molecular weight (Mw) is between about 2,000 to about 80,000.

First claim

What is claimed is:

1. A polythioaminal of the formula:

wherein each instance of R is independently hydrogen or an electron withdrawing group, n is an integer, and the polythioaminal has a number average molecular weight (Mn) or weight average molecular weight (Mw) between about 2,000 to about 80,000.

2. The polythioaminal of claim 1 , wherein the —NH— moiety is para- to the —S— moiety.

3. The polythioaminal of claim 1 , wherein at least one of the electron withdrawing groups is ortho- and/or para- to the —NH— moiety.

4. The polythioaminal of claim 1 , wherein at least one of the electron withdrawing groups is independently selected from the group consisting of —F, —CF 3 , and —NO 2 .

5. The polythioaminal of claim 3 , wherein at least one of the electron withdrawing groups is independently selected from the group consisting of —F, —CF 3 , and —NO 2 .

6. The polythioaminal of claim 1 , wherein the number average molecular weight (Mn) or weight average molecular weight (Mw) is between about 15,000 to about 20,000.

7. A substrate comprising the polythioaminal of claim 1 covalently bonded to a substrate.

8. The polythioaminal of claim 1 , wherein the polythioaminal is selected from the group consisting of:

9. The polythioaminal of claim 1 , wherein the polythioaminal is prepared by mixing a benzothiazole with a reducing agent to yield an aminothiophenol which is then mixed with paraformaldehyde to yield a thiophenol imine.

10. The polythioaminal of claim 9 , wherein the polythioaminal is a product of self-polymerization which occurs by nucleophilic addition of a thiol nucleophile of a first thiophenol imine with the electrophilic carbon of the imine moiety of a second thiophenol imine.

11. The polythioaminal of claim 9 , wherein the polythioaminal is formed by a reaction which occurs between about 30° C. to about 120° C.

12. The polythioaminal of claim 9 , wherein the polythioaminal is formed by a reaction which occurs at room temperature.

13. The polythioaminal of claim 1 , wherein the polythioaminal is prepared by mixing a substituted aminothiophenol with paraformaldehyde to yield a thiophenol imine.

14. The polythioaminal of claim 13 , wherein the polythioaminal is a product of self-polymerization which occurs by nucleophilic addition of a thiol nucleophile of a first thiophenol imine with the electrophilic carbon of the imine moiety of a second thiophenol imine.

15. The polythioaminal of claim 14 , wherein the polythioaminal is formed by a reaction which occurs between about 30° C. to about 120° C.

16. The polythioaminal of claim 14 , wherein the polythioaminal is formed by a reaction which occurs at room temperature.

17. The polythioaminal of claim 1 , wherein each phenyl ring is mono-substituted with an R group.

18. The polythioaminal of claim 1 , wherein each phenyl ring is di-substituted with an R group.

19. The polythioaminal of claim 1 , wherein each phenyl ring is tri-substituted with an R group.

20. The polythioaminal of claim 1 , wherein each phenyl ring is tetra-substituted with an R 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

• C08G75/0272 Primary

  using other sulfur sources · CPC title

• C08G75/0236

  containing atoms other than carbon or sulfur in a linkage between arylene groups · CPC title