Bio-based acrylic monomers

Patent metadata

Field	Value
Publication number	US-10315985-B2
Application number	US-201515502342-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Aug 8, 2014
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

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 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 acrylamide group is esterically linked, directly or indirectly, to the fatty carbonyl group.

2. The bio-based acrylic monomer of claim 1 having formula (I):

wherein R is a fatty chain derived from a plant oil or an animal fat;
R 1 and R 3 are each independently H, an aliphatic group, or an aromatic group; and
R 2 is a divalent aliphatic group or aromatic group.

3. The bio-based acrylic monomer of claim 2 wherein R 1 is H or a (C 1 -C 10 )alkyl.

4. The bio-based acrylic monomer of claim 2 wherein R 2 is a (C 1 -C 10 )alkylene, an alkylene glycol, or a polyalkylene glycol.

5. The bio-based acrylic monomer of claim 2 wherein R 3 is H or a (C 1 -C 10 )alkyl.

6. The bio-based acrylic monomer of claim 1 wherein the fatty acyl group comprises a C 5 -C 21 alkyl group or a C 5 -C 21 alkenyl group.

7. The bio-based acrylic monomer of claim 1 wherein the fatty acyl group comprises 1, 2, 3, 4, 5 or 6 double bonds.

8. The bio-based acrylic monomer of claim 1 wherein the fatty acyl group comprises a fatty chain derived from a plant oil or an animal fat.

9. The bio-based acrylic monomer of claim 8 wherein the plant oil is selected from the group consisting of soybean oil, high oleic soybean oil, linseed oil, flaxseed oil, sunflower oil, safflower oil, canola oil, corn oil, cashew nut oil, olive oil, peanut oil, palm oil, sesame oil, cottonseed oil, rapeseed oil, walnut oil, almond oil, coconut oil, or any combination thereof.

10. The bio-based acrylic monomer of claim 1 wherein the fatty acyl group comprises a fatty chain derived from a fatty acid selected from the group consisting of oleic, linoleic, linolenic, ricinoleic, myristoleic, palmitoleic, elaidic, euric, arachidonic, eleasteric, stearic, palmitic, arachidic, myristic, lauric, caprylic and capric acids.

11. The bio-based acrylic monomer of claim 1 wherein the fatty acyl group comprises at least one functional group selected from the group consisting of an epoxy group, an acrylic group, and an alcohol group.

12. A method of making the bio-based acrylic monomer of claim 1 comprising:
a mixing step comprising
(i) mixing a bio-derived triglyceride, a hydroxy functional acrylamide or a hydroxy functional methacrylamide, and a catalyst to yield a mixture; or
(ii) mixing a bio-derived fatty ester, at least one of an acrylamide alcohol, an acrylamide ester, a methacrylamide alcohol, or a methacrylamide ester, and a catalyst to yield a mixture;

heating the mixture at a temperature between about 25° C.-60° C. for about 2-25 hours;
separating the resulting monomers from the remaining components of the mixture.

13. The method of claim 12 wherein the mixture further comprises a cosolvent of up to 50% wt.

Assignees

• Voronov Andriy
• Tarnavchyk Ihor
• Ndsu Res Foundation

Inventors

• Voronov Andriy
• Tarnavchyk Ihor

Classifications

• 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

• C09D133/24

  Homopolymers or copolymers of amides or imides · CPC title

• C07C231/12

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

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title