Rosin-derived cationic compounds and polymers

Patent metadata

Field	Value
Publication number	US-9357775-B2
Application number	US-201414542769-A
Country	US
Kind code	B2
Filing date	Nov 17, 2014
Priority date	Feb 15, 2011
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

Methods for forming rosin-derived cationic compounds are provided. The method can include attaching a cationic group to a conjugated diene on a hydrophenathrene-based ring of a resin acid (e.g., levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof) to form a rosin-derived cationic compound. Attaching the cationic group to the conjugated diene on the hydrophenathrene-based ring of the resin acid can be achieved via a Diels-Alder reaction of a dienophile with the hydrophenathrene-based ring of the resin acid. Rosin-derived cationic compounds are also provided. The rosin-derived cationic compound can include a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the rosin-derived cationic compound further comprises a carboxylic acid group.

First claim

What is claimed:

1. A rosin-derived polymer formed via polymerization of a rosin-derived cationic compound, wherein the rosin-derived cationic compound comprises a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the cationic group comprises an antimicrobial, and wherein the resin acid of the rosin-derived cationic compound further comprises a carboxylic acid group, and further wherein the resin acid of the rosin-derived cationic compound further comprises a polymerizable group attached to the resin acid via the carboxylic acid group.

2. The rosin-derived polymer as in claim 1 , wherein the rosin derived polymer has a polydispersity index of about 1 to about 1.5.

3. A rosin-derived copolymer formed via polymerization of a rosin-derived cationic compound and a second monomer, wherein the rosin-derived cationic compound comprises a cationic group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the cationic group comprises an antimicrobial, and wherein the resin acid of the rosin-derived cationic compound further comprises a carboxylic acid group, and further wherein the resin acid of the rosin-derived cationic compound further comprises a polymerizable group attached to the resin acid via the carboxylic acid group.

4. The rosin-derived copolymer as in claim 3 , wherein the second monomer is a degradable monomer.

5. A rosin-derived compound comprising a polymerizable group attached to a conjugated diene on a hydrophenathrene-based ring of a resin acid, wherein the polymerizable group comprises a vinyl group or a strained ring functional group.

6. The rosin-derived compound as in claim 5 , wherein the resin acid comprises levopimaric acid, abietic acid, dehydroabietic acid, or a mixture thereof.

7. The rosin-derived compound as in claim 5 , wherein the polymerizable group comprises a vinyl group.

8. The rosin-derived compound as in claim 7 , wherein the vinyl group is an acrylate group or a methacrylate group.

9. The rosin-derived compound as in claim 5 , wherein the polymerizable group comprises a strained ring functional group.

10. The rosin-derived compound as in claim 9 , wherein the strained ring functional group is a cyclic ester group, a norbornene group, or a cyclopentene group.

11. The rosin-derived compound as in claim 9 , wherein the strained ring functional group is a caprolactone group.

12. The rosin-derived compound as in claim 9 , wherein the strained ring functional group is a lactide group.

13. A rosin-derived polymer formed via polymerization of the rosin-derived compound of claim 5 .

14. The rosin-derived compound as in claim 5 , wherein the resin acid of the rosin-derived cationic compound further comprises a carboxylic acid group.

15. The rosin-derived compound as in claim 5 , wherein the resin acid of the rosin-derived cationic compound further comprises a second polymerizable group attached to the resin acid via its carboxylic acid group.

16. A rosin-derived polymer formed via polymerization of the rosin-derived compound of claim 15 .

17. The rosin-derived polymer as in claim 1 , wherein the rosin-derived polymer has a molecular weight of about 2,000 g/mol to about 1,000,000 g/mole.

18. The rosin-derived polymer as in claim 3 , wherein the rosin derived polymer has a polydispersity index of about 1 to about 1.5.

19. The rosin-derived polymer as in claim 3 , wherein the rosin-derived polymer has a molecular weight of about 2,000 g/mol to about 1,000,000 g/mole.

20. The rosin-derived polymer as in claim 3 , wherein the rosin-derived cationic compound is about 10% by weight to about 90% by weight of the rosin-derived polymer.

Assignees

• Univ South Carolina

Inventors

• Tang Chuanbing
• Wang Jifu
• Decho Alan W
• Chen Yung Pin

Classifications

• C08F120/40

  Esters of unsaturated alcohols {, e.g. allyl (meth)acrylate} · CPC title

• C08G81/00

  Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42}) · CPC title

• A01N43/10

  with sulfur as the ring hetero atom · CPC title

• C08F240/00

  Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins · CPC title

• A01N57/22

  containing aromatic radicals · CPC title