Tackifier compounds and methods of using the same

Patent metadata

Field	Value
Publication number	US-10280241-B2
Application number	US-201815881117-A
Country	US
Kind code	B2
Filing date	Jan 26, 2018
Priority date	Oct 15, 2012
Publication date	May 7, 2019
Grant date	May 7, 2019

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 method of making a tackifier compound, comprising:
contacting
a compound having the structure

and
at least one acid anhydride having the structure

to provide a tackifier compound having the structure

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 substituted or unsubstituted;
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 substituted or unsubstituted; and
fused rings A and B are each independently substituted or unsubstituted.

2. The method of claim 1 , wherein m=n=1.

3. The method of claim 1 , wherein the anhydride is chosen from succinic anhydride, glutaric anhydride, and maleic anhydride.

4. The method of claim 1 , wherein rings A and B form a ring system chosen from isosorbide, isomannide, and isoidide.

5. The method of claim 1 , wherein R′ is chosen from ethylene, propylene, and ethenylene.

6. The method of claim 1 , wherein R′ is —OH.

7. The method of claim 1 , wherein R 1 is

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

9. The method of claim 1 , wherein the compound is

10. The method of claim 1 , wherein the compound is chosen from

11. The method of claim 1 , wherein the method is a method of making a polymer, wherein at least one R′ is (C 2 -C 10 )alkenylene or (C 2 -C 10 )alkynylene, the method further comprising crosslinking the tackifier compound to provide a polymer comprising a repeating unit having the structure

or a salt thereof;
wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

or a salt thereof, wherein at each occurrence R″ is independently a (C 2 -C 10 )alkanylene bonded to at least one of a repeating unit and an end-blocking unit of the polymer at two locations, wherein R″ is substituted or unsubstituted.

12. The method of claim 11 , wherein the repeating unit has a structure chosen from:

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

13. The method of claim 11 , wherein the repeating unit has the structure:

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

14. The method of claim 11 , wherein R″ is an alkanylene bonded to at least one of a repeating unit and an end-blocking unit of the polymer at two locations and is chosen from ethylene, propylene, butylene, or pentylene.

15. The method of claim 11 , wherein the repeating unit has a structure chosen from:

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

16. The method of claim 11 , wherein the repeating unit has the structure

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

17. The method of claim 11 , wherein the repeating unit has the structure:

18. The method of claim 11 , wherein the repeating unit has a structure chosen from:

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

19. The method of claim 11 , wherein the repeating unit has a structure chosen from:

wherein at each occurrence R 4 is independently selected from —OH, —OR 3 ,

20. The method of claim 11 , wherein the repeating unit has a structure chosen from:

Assignees

• Univ Iowa State Res Found Inc

Inventors

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

Classifications

• H04B2203/5425

  improving S/N by matching impedance, noise reduction, gain control · CPC title

• C08G18/3218

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

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C08G18/771

  oxygen · CPC title

• B60L53/20

  characterised by converters located in the vehicle · CPC title