Polycarbodiimides having onium salt groups

Patent metadata

Field	Value
Publication number	US-9631045-B2
Application number	US-37010009-A
Country	US
Kind code	B2
Filing date	Feb 12, 2009
Priority date	Feb 12, 2009
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

Disclosed are polycarbodiimides having onium salt groups, as well as methods for their production.

First claim

We claim:

1. A polycarbodiimide comprising an unbranched backbone and terminal onium salt groups, wherein the terminal onium salt groups comprise a trialkyl onium group and a halogen counterion.

2. The polycarbodiimide of claim 1 , wherein the polycarbodiimide has the structure:

in which:
(a) each R is an unbranched, divalent linking group and each may be the same or different;
(b) R 1 is A when y is 1 and is the residue of an active hydrogen-containing chain extender when y is at least 2;
(c) n has a value of at least 2;
(d) y has a value of 1 to 4; and
(e) each A is represented by the structure:

in which:
(1) each X is N or P and may be the same or different;
(2) each Y is a halogen and may be the same or different;
(3) each Z is O, NH, or Sand may be the same or different;
(4) each R 3 is an unbranched, divalent linking group and may be the same or different; and
(5) each R 4 is a monovalent hydrocarbon group and may be the same or different.

3. The polycarbodiimide of claim 1 , wherein the polycarbodiimide has the structure:

in which:
(a) each R is an unbranched, divalent linking group and each may be the same or different;
(b) each R 2 is an unbranched, linking group and may be the same or different;
(c) each X is O, NH, or S and may be the same or different;
(d) n has a value of at least 2;
(e) p has a value of 1 to 3; and
(f) each A is represented by the structure:

in which:
(1) each X is N or P and may be the same or different;
(2) each Y is a halogen and may be the same or different;
(3) each Z is O, NH, or S and may be the same or different;
(4) each R 3 is an unbranched, divalent linking group and may be the same or different; and
(5) each R 4 is a monovalent hydrocarbon group and may be the same or different.

4. The polycarbodiimide of claim 2 , wherein y is 1.

5. The polycarbodiimide of claim 2 , wherein n has a value of 2 to 10.

6. The polycarbodiimide of claim 3 , wherein n has a value of 2 to 10.

7. The polycarbodiimide of claim 1 , wherein the halogen counterion comprises a chlorine ion.

8. The polycarbodiimide of claim 1 , wherein the trialkyl onium group comprises trimethylammonium.

9. The polycarbodiimide of claim 1 , wherein the polycarbodiimide comprises a unit having the general structure:

wherein:
(a) X is N or P;
(b) Y is an anion;
(c) R 6 is a divalent linking group; and
(d) each R 7 is a monovalent hydrocarbon group and may be the same or different.

10. The polycarbodiimide of claim 9 , wherein X is N.

11. The polycarbodiimide of claim 9 , wherein Y is a halogen.

12. A polycarbodiimide comprising an unbranched backbone and terminal trialkyl onium salt groups.

13. The polycarbodiimide of claim 12 , wherein the polycarbodiimide comprises repeat units having the general structure:

wherein:
(a) X is N or P;
(b) Y is an anion;
(c) R 6 is a divalent linking group; and
(d) each R 7 is a monovalent hydrocarbon group and may be the same or different.

14. The polycarbodiimide of claim 13 , wherein X is N.

15. The polycarbodiimide of claim 13 , wherein Y is a halogen.

16. The polycarbodiimide of claim 12 , wherein the polycarbodiimide has the structure (VIII) or (IX):

in which:
(a) each R 8 is an unbranched, divalent linking group and each may be the same or different;
(b) R 9 is A when y is 1 and is the residue of an active hydrogen-containing chain extender when y is at least 2;
(c) each R 10 is an unbranched, linking group and may be the same or different;
(d) each X is O, NH, or S and may be the same or different;
(e) each n has a value of at least 1 and may be the same or different wherein at least one n has a value of at least 2;
(f) y has a value of 1 to 4;
(g) p has a value of 1 to 3;
(h) each A represents a terminal group;
(i) each A 1 represents a unit having the general structure (VIII) or a —N═C═N— unit; and
(j) each A 2 represents a unit having the structure:

wherein R 8 is as defined above.

17. The polycarbodiimide of claim 16 , wherein n has a value of 2 to 10.

18. The polycarbodiimide of claim 2 , wherein the monovalent hydrocarbon group comprises one of a methyl group, an ethyl group, a propyl group, a isopropyl group, a iso-butyl group, a t-butyl group, a n-butyl group, a pentyl group, a hexyl group, a heptyl group, a octyl group, a nonyl group, a decyl group, and a dodecyl group.

19. The polycarbodiimide of claim 3 , wherein the monovalent hydrocarbon group comprises one of a methyl group, an ethyl group, a propyl group, a isopropyl group, a iso-butyl group, a t-butyl group, a n-butyl group, a pentyl group, a hexyl group, a heptyl group, a octyl group, a nonyl group, a decyl group, and a dodecyl group.

20. The polycarbodiimide of claim 9 , wherein the monovalent hydrocarbon group comprises one of a methyl group, an ethyl group, a propyl group, a isopropyl group, a iso-butyl group, a t-butyl group, a n-butyl group, a pentyl group, a hexyl group, a heptyl group, a octyl group, a nonyl group, a decyl group, and a dodecyl group.

Assignees

• Chasser Anthony M
• Fitzgerald Lawrence J
• Kalsani Venkateshwarlu
• Ppg Ind Ohio Inc

Inventors

• Chasser Anthony M
• Fitzgerald Lawrence J
• Kalsani Venkateshwarlu

Classifications

• C08G18/095

  oligomerisation to carbodiimide or uretone-imine groups · CPC title

• C08G18/285

  Nitrogen containing compounds · CPC title

• C08G18/797 Primary

  containing carbodiimide and/or uretone-imine groups · CPC title

• Y10S525/907

  Polycarbodiimide · CPC title

• C08G18/0814

  containing ammonium groups or groups forming them · CPC title