# US 9,518,167 B2 · Bioderived based plasticizers

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- Number: US 9,518,167 B2
- Document ID: US9518167B2
- Status: Granted
- Kind: B2
- Application number: 14/636,336
- Filed: 2015-03-03
- Published: 2016-09-08
- Granted: 2016-12-13
- Earliest claimed: 2015-03-03
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Dylan J. Boday; Joseph Kuczynski; Jason T. Wertz; Jing Zhang
- Web page: https://patentgrep.com/patent/US9518167B2

## CPC

- C07D 307/42: Singly bound oxygen atoms
- C08K 5/1535: Five-membered rings
- C08K 5/0016: {Plasticisers}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A bioderived based plasticizer is produced by reacting a bioderived diol (and/or a bioderived alcohol) and a bioderived carboxylic acid in the presence of N,N′-dicyclohexylcarbodiimide (DCC), wherein the bioderived carboxylic acid includes a hydrolyzed oil. The bioderived carboxylic acid (e.g., linoleic acid, α-linolenic acid, oleic acid, and mixtures thereof) may be produced by hydrolyzing a triglyceride, such as canola oil, linseed oil, soybean oil, and mixtures thereof. In one embodiment of the present invention, a bioderived based plasticizer is produced by reacting 2,5-bis-(hydroxymethyl)furan and α-linolenic acid in the presence of DCC. In some embodiments of the present invention, the bioderived based plasticizer is blended into one or more polymers.

## Claims

### Claim 1

A method of producing a bioderived based plasticizer, comprising:
reacting a bioderived diol and a bioderived carboxylic acid in the presence of N,N′-dicyclohexylcarbodiimide (DCC), wherein the bioderived carboxylic acid includes a hydrolyzed oil.

### Claim 2 (depends on 1)

The method as recited in claim 1, wherein the bioderived diol is selected from the group consisting of 2,5-bis(hydroxymethyl)furan, 2,5-bis(hydroxymethyl)tetrahydrofuran, isosorbide, and mixtures thereof.

### Claim 3 (depends on 1)

The method as recited in claim 1, wherein the bioderived carboxylic acid includes a hydrolyzed oil having a chemical structure represented by the following formula:
wherein R is aliphatic and contains from 5 to 25 carbon atoms.

### Claim 4 (depends on 3)

The method as recited in claim 3, wherein the bioderived carboxylic acid includes a hydrolyzed oil selected from the group consisting of linoleic acid, α-linolenic acid, oleic acid, and mixtures thereof.

### Claim 5 (depends on 4)

The method as recited in claim 4, wherein the bioderived diol includes 2,5-bis(hydroxymethyl)furan.

### Claim 6 (depends on 1)

The method as recited in claim 1, further comprising:
hydrolyzing a triglyceride to produce the bioderived carboxylic acid.

### Claim 7 (depends on 6)

The method as recited in claim 6, wherein the triglyceride is selected from the group consisting of canola oil, corn oil, cottonseed oil, linseed oil, peanut oil, safflower oil, soybean oil, sunflower oil, and mixtures thereof.

### Claim 8 (depends on 6)

The method as recited in claim 6, wherein the triglyceride is selected from the group consisting of canola oil, linseed oil, soybean oil, and mixtures thereof.

### Claim 9 (depends on 8)

The method as recited in claim 8, wherein the triglyceride includes linseed oil.

### Claim 10 (depends on 8)

The method as recited in claim 8, wherein the bioderived diol is selected from the group consisting of 2,5-bis(hydroxymethyl)furan, 2,5-bis(hydroxymethyl)tetrahydrofuran, isosorbide, and mixtures thereof.

### Claim 11 (depends on 10)

The method as recited in claim 10, wherein the triglyceride includes linseed oil, and wherein the bioderived diol includes 2,5-bis(hydroxymethyl)furan.

### Claim 12

A method of producing a bioderived based plasticizer, comprising:
hydrolyzing a triglyceride to produce a bioderived carboxylic acid, wherein the triglyceride is selected from the group consisting of canola oil, corn oil, cottonseed oil, linseed oil, peanut oil, safflower oil, soybean oil, sunflower oil, and mixtures thereof;
reacting a bioderived diol and the bioderived carboxylic acid in the presence of N,N′-dicyclohexylcarbodiimide (DCC), wherein the bioderived diol is selected from the group consisting of 2,5-bis(hydroxymethyl)furan, 2,5-bis(hydroxymethyl)tetrahydrofuran, isosorbide, and mixtures thereof.

### Claim 13

A method of producing a bioderived based plasticizer, comprising:
reacting a bioderived diol and a bioderived carboxylic acid in the presence of N,N′-dicyclohexylcarbodiimide (DCC), wherein the bioderived diol is selected from the group consisting of 2,5-bis(hydroxymethyl)furan, 2,5-bis(hydroxymethyl)tetrahydrofuran, isosorbide, and mixtures thereof, and wherein the bioderived carboxylic acid includes a hydrolyzed oil selected from the group consisting of linoleic acid, a-linolenic acid, oleic acid, and mixtures thereof.