Adhesives from renewable feedstocks

Patent metadata

Field	Value
Publication number	US-10316137-B2
Application number	US-201615552429-A
Country	US
Kind code	B2
Filing date	Feb 19, 2016
Priority date	Feb 21, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Poly[(3,4-dihydroxymandelic acid)-co-(lactic acid)] can be produced from renewable feedstocks, possesses tunable degradation, and can achieve adhesion strengths rivaling the performance of existing glues and adhesives. In one aspect, a polymer is presented. The polymer includes poly[(3,4-dihydroxymandelic acid)-co-(lactic acid)]. The polymer can be an adhesive. The adhesive is configured to have tunable degradation. The polymer is derived from renewable resources. The renewable resources can include any one of or a combination of starch, cellulose, hemicellulose, lignin, chitin, polyphenols, poly (isoprene), suberin, polyterpenes, polyterpenoids, polyhydroxyalkanoates, rosin-based polymers, triglyceride-based polymers, alginates, and/or proteins.

First claim

The invention claimed is:

1. A process for preparing a biomimetic polymer comprising the steps of
a. heating 3,4-(methylenedioxy)mandelic acid to afford an oligomer thereof;
b. preparing polylactic acid (PLA) from a renewable resource;
c. melting PLA and oligomer of 3,4-(methylenedioxy)mandelic acid at an elevated temperature in the presence of tin(II) 2-ethylhexanoate and a strong acid at a molar ratio of about 1:1 under reduced pressure; and
d. removing methylene moiety of phenolic hydroxyl protection using a strong acid to afford said biomimetic polymer, wherein said strong acid used to remove methylene protection is p-toluenesulfonic acid in an amount of about 10% weight of reaction mixture.

2. The process of claim 1 , wherein said biomimetic polymer is poly[(3,4-dihydroxymandelic acid)-co-(lactic acid)].

3. The process of claim 2 , wherein biomimetic polymer is an adhesive.

4. The process of claim 1 , wherein said oligomer of 3,4-(methylenedioxy)mandelic acid comprises about four monomer units.

5. The process of claim 1 , wherein said strong acid is p-toluenesulfonic acid (TSA).

6. The process of claim 1 , wherein said natural resource is selected from the group consisting of starch, cellulose, hemicellulose, lignin, chitin, polyphenols, suberin, poly(isoprene), polyterpenes, polyterpenoids, polyhydroxyalkanoates, rosin-based polymers, triglyceride-based polymers, alginates, and proteins of nature.

Assignees

• Purdue Research Foundation

Inventors

• Wilker Jonathan James
• Jenkins Courtney Lynn

Classifications

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title

• C09J105/08

  Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof · CPC title

• C08G63/06 Primary

  derived from hydroxycarboxylic acids · CPC title

• C09J189/00

  Adhesives based on proteins; Adhesives based on derivatives thereof · CPC title

• C09J103/02

  Starch; Degradation products thereof, e.g. dextrin · CPC title