Bio-based acrylic monomers and polymers thereof

Patent metadata

Field	Value
Publication number	US-10584094-B2
Application number	US-201916395755-A
Country	US
Kind code	B2
Filing date	Apr 26, 2019
Priority date	Aug 8, 2014
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

The invention provides a bio-based acrylic monomer, particularly a plant oil-based acrylic monomer, which is well-suited for emulsion polymerization and latex formation in aqueous medium. Polymers and copolymers formed from the bio-based acrylic monomer are also provided. The invention further provided methods for making the monomer from bio-based triglycerides or fatty esters.

First claim

What is claimed is:

1. A polymer comprising at least one bio-based acrylic monomer comprising:
a bio-derived fatty acyl group comprising a carbonyl group, wherein the fatty acyl group comprises at least 1 double bond; and
an acrylic group, wherein the acrylic group comprises an acrylamide group or a methacrylamide group;
wherein the acrylic group is esterically linked, directly or indirectly, to the fatty carbonyl group.

2. The polymer of claim 1 wherein the bio-based acrylic monomer has formula (I):

wherein R is a fatty chain derived from a plant oil or an animal fat;
R1 and R3 are each independently H, an aliphatic group, or an aromatic group; and
R2 is a divalent aliphatic group or aromatic group.

3. The polymer of claim 1 comprising a homopolymer of the bio-based acrylic monomer or a copolymer further comprising at least one comonomer.

4. The polymer of claim 3 wherein the comonomer comprises a vinyl comonomer.

5. The polymer of claim 3 wherein the comonomer is selected from the group consisting of an acrylate, a methacrylate, an acrylamide, a methacrylamide, and an acrylonitrile.

6. The polymer of claim 3 wherein the comonomer is selected from the group consisting of an alkyl acrylate and an alkyl methacrylate.

7. The polymer of claim 3 wherein the comonomer is selected from the group consisting of a 1,3-butadiene, a butyl acrylate, a butyl methacrylate, an ethyl acrylate, a hydroxyethyl acrylate, an isoprene, a maleic anhydride, a methyl acrylate, a methyl methacrylate, a 2-ethylhexyl methacrylate, a styrene, a vinyl acetate, a vinyl ether, a vinyl pyridine, a vinyl chloride, a poly(ethylene glycol) methacrylate, a poly(ethylene glycol) methyl ether methacrylate, a poly(ethylene glycol) methyl ether acrylate, a phenyl ether acrylate, and a polyfunctional vinyl monomer.

8. The polymer of claim 1 formed in a free radical polymerization reaction.

9. A latex comprising an emulsion comprising a polymer comprising the bio-based acrylic monomer of claim 1 .

10. A waterborne coating comprising a polymer comprising the bio-based acrylic monomer of claim 1 .

11. A paint, adhesive, thermoplastic, plastic, resin, emulsion, surfactant, gel, coating or oil comprising a polymer comprising the bio-based acrylic monomer of claim 1 .

12. An article comprising a latex, waterborne coating, paint, adhesive, thermoplastic, plastic, resin, emulsion, surfactant, gel, coating or oil comprising a polymer comprising the bio-based acrylic monomer of claim 1 .

13. A personal care product comprising the polymer of claim 1 .

14. An industrial cleaning product comprising the polymer of claim 1 .

15. The polymer of claim 2 wherein R 1 is H or a (C 1 -C 10 )alkyl.

16. The polymer of claim 2 wherein R 2 is a (C 1 -C 10 )alkylene, an alkylene glycol, or a polyalkylene glycol.

17. The polymer of claim 2 wherein R 3 is H or a (C 1 -C 10 )alkyl.

18. The polymer of claim 1 wherein the fatty acyl group comprises a C 5 -C 21 alkyl group or a C 5 -C 21 alkenyl group.

19. The polymer of claim 1 wherein the fatty acyl group comprises 1, 2, 3, 4, 5 or 6 double bonds.

Assignees

• Voronov Andriy
• Tarnavchyk Ihor
• Ndsu Res Foundation

Inventors

• Voronov Andriy
• Tarnavchyk Ihor

Classifications

• C09D133/24

  Homopolymers or copolymers of amides or imides · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C233/20 Primary

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C08F220/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title