Tackifier compounds and methods of using the same

Patent metadata

Field	Value
Publication number	US-9688794-B2
Application number	US-201314434719-A
Country	US
Kind code	B2
Filing date	Oct 15, 2013
Priority date	Oct 15, 2012
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

The present invention relates to tackifier compounds and methods of using the same. In various embodiments, the present invention provides a tackifier compound including independently substituted or unsubstituted fused rings A and B each independently chosen from (C 5 -C 10 )cycloalkyl and (C 2 -C 10 )heterocyclyl. Fused ring A is substituted with (R 1 ) 1-8 and fused ring B is substituted with —(OC(O)R′C(O)R 2 ) 1-8 . At each occurrence R′ is independently chosen from (C 2 -C 10 )alkanylene, (C 2 -C 10 )alkenylene, (C 2 -C 10 )alkynylene, C 5 -C 20 (arylene), and (C 1 -C 20 )heteroarylene, wherein R′ is unsubstituted or substituted. At each occurrence R 1 is independently selected from —OH, —OR 3 , and —OC(O)R′C(O)R 2 . At each occurrence R 2 is independently chosen from —OH, —OR 3 , —NH 2 , —NHR 3 , and —NR 3 2 . At each occurrence R 3 is independently chosen from (C 1 -C 10 )alkanyl, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, C 5 -C 20 (aryl), and (C 1 -C 20 )heteroaryl, wherein R 3 is unsubstituted or substituted.

First claim

What is claimed is:

1. A tackifier compound having the structural formula

or a salt thereof;
wherein fused rings A and B are each independently chosen from (C 5 -C 10 )cycloalkyl and (C 2 -C 10 )heterocyclyl;
m and n are each independently 1-8;
at each occurrence R 1 is independently selected from —OH, —OR 3 , and

at each occurrence R′ is independently chosen from (C 2 -C 10 )alkanylene, (C 2 -C 10 )alkenylene, (C 2 -C 10 )alkynylene, C 5 -C 20 (arylene), and (C 1 -C 20 )heteroarylene, wherein R′ is unsubstituted or substituted;
at each occurrence R 2 is independently chosen from —OH, —OR 3 , —NH 2 , —NHR 3 , and —NR 3 2 ;
at each occurrence R 3 is independently chosen from (C 1 -C 10 )alkanyl, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, C 5 -C 20 (aryl), and (C 1 -C 20 )heteroaryl, wherein R 3 is unsubstituted or substituted; and
fused rings A and B are each independently unsubstituted or substituted, wherein rings A and B form a ring system chosen from isosorbide, isomannide, and isoidide.

2. The tackifier compound of claim 1 , wherein R 1 is —OH.

3. The tackifier compound of claim 1 , wherein R 1 is

4. The tackifier compound of claim 1 , wherein R 2 is —O(C 1 -C 5 )alkyl or —OH.

5. The tackifier compound of claim 1 , wherein at each occurrence R′ is independently (C 1 -C 5 )alkylene, (C 5 -C 10 )aryl, or (C 2 -C 5 )alkenylene.

6. The tackifier compound of claim 1 , wherein at each occurrence R′ is independently —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, o-phenylene, or —CH═CH—.

7. The tackifier compound of claim 1 , wherein the compound is

8. The tackifier compound of claim 1 , wherein the compound is

9. A reaction product of the tackifier compound of claim 1 .

10. A composition comprising the tackifier compound of claim 1 and a free-radical initiator or a transition metal catalyst.

11. A system comprising:
the tackifier compound of claim 1 ; and
a first substrate;
wherein the tackifier compound is bonded to the first substrate.

12. A method of using the tackifier compound of claim 1 comprising contacting the tackifier compound to a first substrate such that the tackifier is bonded to the first substrate.

13. The tackifier compound of claim 1 , wherein the compound is chosen from

14. The tackifier compound of claim 1 , wherein the compound is chosen from

15. The tackifier compound of claim 1 , wherein the compound is chosen from

16. The tackifier compound of claim 1 , wherein the compound is chosen from

17. The tackifier compound of claim 1 , wherein the compound is chosen from

18. The tackifier compound of claim 1 , wherein the compound is chosen from

19. The tackifier compound of claim 1 , wherein the compound is chosen from

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Chen Jason Shih-Hao
• Kessler Michael Richard
• Zenner Michael Dennis

Classifications

• C08L75/08

  from polyethers · CPC title

• C08F122/20 Primary

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• C09J135/02

  Homopolymers or copolymers of esters (C09J135/06, C09J135/08 take precedence) · CPC title

• C08G18/3218

  containing cyclic groups having at least one oxygen atom in the ring · CPC title

• B60L53/20

  characterised by converters located in the vehicle · CPC title