Polythioaminals with tunable modulus

Patent metadata

Field	Value
Publication number	US-9884940-B2
Application number	US-201615153079-A
Country	US
Kind code	B2
Filing date	May 12, 2016
Priority date	May 12, 2016
Publication date	Feb 6, 2018
Grant date	Feb 6, 2018

Abstract

Compounds include boronate ester polythioaminals with substituents that include hydrogen, fluorine or substituted or unsubstituted alkyls. The boronate ester polythioaminals have number average molecular weight or weight average molecular weight between about 2,000 to about 160,000.

First claim

What is claimed is:

1. A material comprising a compound from the group consisting of formulas (I), (II), (III), (IV), and salts thereof:

wherein:
each instance of R 2 is independently selected from the group consisting of hydrogen, halo, aryl, alkoxyl, cycloalkyl, heterocyclyl, —NH 2 , and substituted or unsubstituted alkyl;
each instance of R 3 and R 5 is independently selected from the group consisting of substituted or unsubstituted alkyl, aryl, cycloalkyl, or heterocyclyl or R 3 and R 5 combine to form a 5- or 6-membered cycloalkyl or heterocyclyl;
each instance of R 4 is independently a substituted or unsubstituted methylene;
M + is a cation; and
each of n, m, and q is a positive integer and the number average molecular weight or weight average molecular weight of the polythioaminals of each of formulas (I), (II), (III), and (IV) is between about 2,000 to about 160,000.

2. The material of claim 1 , wherein each instance of M + is independently selected from the group consisting of Na + , K + , Li + , Mg 2+ , and Ca 2+ .

3. The material of claim 1 , wherein at least one of R 3 and R 5 is substituted with alkyl, hydroxyl, aryl, alkoxyl, halo, cycloalkyl, or heterocyclyl.

4. The material of claim 1 , wherein the compound is selected from the group consisting of:

and R 4 is substituted with one or more of alkyl, aryl, alkoxyl, halo, cycloalkyl, or heterocyclyl.

5. The material of claim 1 , wherein R 2 is substituted with one or more of alkyl, aryl, alkoxyl, halo, cycloalkyl, heterocyclyl, or —NH 2 .

6. The material of claim 1 , wherein the number average molecular weight or weight average molecular weight of the compounds of each of formulas (I), (II), (III), and (IV) is between about 15,000 to about 40,000.

7. The material of claim 1 , wherein R 3 and R 5 combine to form a hydroxyl substituted 5- or 6-membered heterocyclyl.

8. The material of claim 7 , wherein the hydroxyl substituted 5- or 6-membered heterocyclyl is selected from the group consisting of:

9. A material comprising a compound from the group consisting of formulas (V), (VI), (VII), (VIII), and salts thereof:

wherein:
each instance of R 2 is independently selected from the group consisting of hydrogen, halo, aryl, alkoxyl, cycloalkyl, heterocyclyl, —NH 2 , and substituted or unsubstituted alkyl;
each instance of R 3 and R 5 is independently selected from the group consisting of substituted or unsubstituted alkyl, aryl, cycloalkyl, or heterocyclyl or R 3 and R 5 combine to form a 5- or 6-membered cycloalkyl or heterocyclyl;
each instance of R 4 is independently a substituted or unsubstituted methylene;
each instance of R 7 is independently selected from the group consisting of substituted or unsubstituted alkyl, aryl, cycloalkyl, heterocyclyl, polyether, and mixtures thereof;
M + is a cation; and
n, m, and q is each a positive integer and the number average molecular weight or weight average molecular weight of the polythioaminals of each of formulas (I), (II), (III), and (IV) is between about 2,000 to about 160,000.

10. The material of claim 9 , wherein the polyether is a glycol.

11. The material of claim 10 , wherein the glycol is polyethylene glycol or polypropylene glycol.

12. The material of claim 9 , wherein R 7 is substituted with at least one substituent selected from the group consisting of alkyl, aryl, alkoxyl, halo, cycloalkyl, and heterocyclyl.

13. The material of claim 9 , wherein each instance of M+ is independently selected from the group consisting of Na + , K + , Li + , Mg 2+ , and Ca 2+ .

14. The material of claim 9 , wherein at least one of R 3 and R 5 is substituted with one or more of alkyl, hydroxyl, aryl, alkoxyl, halo, cycloalkyl, or heterocyclyl.

15. The material of claim 9 , wherein the compound is selected from the group consisting of:

wherein R 4 is substituted with one or more of alkyl, aryl, alkoxyl, halo, cycloalkyl, or heterocyclyl.

16. The material of claim 9 , wherein R 2 is substituted with one or more of alkyl, aryl, alkoxyl, halo, cycloalkyl, heterocyclyl, or —NH 2 .

17. The material of claim 9 , wherein the number average molecular weight or weight average molecular weight of the compounds of each of formulas (I), (II), (III), and (IV) is between about 15,000 to about 40,000.

18. The material of claim 9 , wherein R 3 and R 5 combine to form a hydroxyl substituted 5- or 6-membered heterocyclyl.

19. The material of claim 18 , wherein the hydroxyl substituted 5- or 6-membered heterocyclyl is selected from the group consisting of:

20. The material of claim 18 , wherein the compound is of formula (IX):

Assignees

• IBM

Inventors

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

Classifications

• C08K2003/387

  Borates · CPC title

• C08K3/38

  Boron-containing compounds · CPC title

• C08G75/04 Primary

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

• C08G73/02

  Polyamines · CPC title

• C08G73/0206

  Polyalkylene(poly)amines · CPC title