# US 11,072,694 B1 · Biobased compositions

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- Number: US 11,072,694 B1
- Document ID: US11072694B1
- Status: Granted
- Kind: B1
- Application number: 17/176,874
- Filed: 2021-02-16
- Granted: 2021-07-27
- Earliest claimed: 2021-02-16
- Assignees: Evoco Limited
- Applicants: Evoco Limited
- Inventors: Jason James Robinson; Radu Lucian Vicol; Juri Helmut Moebus; Tristan Calayan; Guerino G. Sacripante
- Web page: https://patentgrep.com/patent/US11072694B1

## CPC

- C08G 18/4288: {modified by higher fatty oils or their acids or by resin acids}
- C08K 5/11: of acyclic polycarboxylic acids
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 69/40: Succinic acid esters
- C07C 69/50: Sebacic acid esters
- C07C 69/708: Ethers
- C07C 69/734: Ethers
- C08G 18/18: containing secondary or tertiary amines or salts thereof
- C08G 18/2063: {having two nitrogen atoms in the condensed ring system}
- C08G 18/3206: {aliphatic}
- C08G 18/3275: {containing two hydroxy groups}
- C08G 18/4238: {derived from dicarboxylic acids and dialcohols}
- C08G 18/4286: {prepared from a combination of hydroxycarboxylic acids and/or lactones with polycarboxylic acids or ester forming derivatives thereof and polyhydroxy compounds}
- C08G 18/664: {with compounds of group C08G18/3203}
- C08G 18/6655: {with compounds of group C08G18/3271}
- C08G 18/73: acyclic
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 18/797: {containing carbodiimide and/or uretone-imine groups}
- C08G 63/16: Dicarboxylic acids and dihydroxy compounds
- C08G 18/14: {Manufacture of cellular products}
- C08G 2110/0008: flexible
- C08G 2110/0066: ≥ 150kg/m3
- C08G 2110/0083: prepared using water as the sole blowing agent
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A composition comprised of a component selected from the group consisting of a biobased bis-alkyl succinate and a biobased bis-alkyl sebacate, each derived, for example, from the esterification of biobased diacid such as succinic acid or sebacic acid, and a biobased alcohol and a biobased polyester.

## Claims

### Claim 1

A composition comprised of a component selected from the group consisting of a biobased bis(cardanol) succinate, a biobased bis(ethoxy-cardanolyl) succinate, a biobased bis(cardanol) sebacate, a biobased bis(ethoxy-cardanolyl) sebacate, and mixtures thereof, and a biobased polyester resin.

### Claim 2 (depends on 1)

The composition of claim 1 wherein said component is a biobased bis(cardanol) succinate.

### Claim 3 (depends on 1)

The composition of claim 1 wherein said component is a biobased bis(cardanol) sebacate.

### Claim 4 (depends on 1)

The composition of claim 1 wherein said biobased polyester resin is selected from the group consisting of poly(1,2-propylene-succinate), poly(1,2-propylene-sebacate), poly(1,3-propylene-succinate), poly(1,3-propylene-sebacate), poly(1,4-butylene-succinate), poly(1,4-butylene-sebacate), poly(1,2-propylene-azeleate), poly(1,2-propylene-azeleate), copoly(1,2-propylene succinate)-copoly(1,3-propylene succinate), copoly(1,2-propylene sebacate)-copoly(1,3-propylene sebacate), poly-12-hydroxy stearate, poly-riciniloate, copoly(1,2-propylene succinate)-copoly(1,2-hydroxy stearate), copoly(1,2-propylene-sebacate)-copoly(12-hydroxy stearate), copoly(1,3-propylene succinate)-copoly(12-hydroxy stearate), copoly(1,3-propylene sebacate)-copoly(12-hydroxy stearate), copoly(1,2-propylene succinate)-copoly(1,2-propylene sebacate), copoly(1,3-propylene succinate)-copoly(1,3-propylene sebacate), terpoly(1,2-propylene succinate)-terpoly(1,3-propylene-succinate)-terpoly(12-hydroxy stearate), copoly(1,2-propylene succinate)-copoly(riciniloate), copoly(1,2-propylene-sebacate)-copoly(riciniloate), copoly(1,3-propylene succinate)-copoly(riciniloate), copoly(1,3-propylene sebacate)-copoly(12-ricinolate), terpoly(1,2-propylenesuccinate)-terpoly(1,3-propylene-succinate)-terpoly(12-hydroxy stearate), and terpoly(1,2-propylene succinate)-terpoly(1,3-propylene-succinate)-terpoly(riciniloate).

### Claim 5 (depends on 1)

The composition of claim 1 wherein said biobased polyester resin comprises random segments represented by:
where:
a is an integer of from about 1 to about 10,
b is an integer of from about 1 to about 18,
m is an integer of from about 10 to about 1000,
n is an integer of from about 0 to about 1000, and
p is an integer of from about 0 to about 1000.

### Claim 6 (depends on 1)

The composition of claim 1 wherein said component is a biobased bis(ethoxy-cardanolyl) succinate.

### Claim 7 (depends on 1)

The composition of claim 1 wherein said component is a biobased bis(ethoxy-cardanolyl) sebacate.

### Claim 8 (depends on 1)

The composition of claim 1 wherein said biobased polyester resin is derived from an organic diacid, an organic diol, and an organic acid-alcohol.

### Claim 9

A plasticizer comprised of a component that is a biobased bis(ethoxy-cardanolyl) sebacate.

### Claim 10 (depends on 9)

The plasticizer of claim 9 derived from the esterification of a biobased diacid and a biobased alcohol, and optionally wherein said biobased diacid is sebacic acid, and said biobased alcohol is ethoxylated cardanol.

### Claim 11

A plasticizer comprised of a component, wherein said component is represented by
wherein n is 1 (succinate) or 9 (sebacate) where each R is selected from the group consisting of cardanylol, and ethoxylated cardanyl, represented by
respectively.

### Claim 12

A polyurethane elastomer derived from a plasticizer comprised of a component selected from the group consisting of a biobased bis(cardanol) succinate, a biobased bis(ethoxy-cardanolyl) succinate, a biobased bis(cardanol) sebacate, a biobased bis(ethoxy-cardanolyl) sebacate, and mixtures thereof, and a) an organic diisocyanate, (b) a biobased polyester resin, (c) a chain extender, (d) a crosslinker, (e) a surfactant, (f) an optional foaming agent, (g) an optional colorant, and (h) a catalyst.

### Claim 13 (depends on 12)

The polyurethane elastomer of claim 12 wherein the foaming agent is present, said colorant is present and is comprised of a dye or a pigment, and wherein said organic diisocyanate is selected from the group consisting of diphenylmethane 4,4′-diisocyanate, isophorone diisocyanate, dicyclohexylmethane 4,4-diisocyanate, hexamethylene 1,6-diisocyanate, naphthalene 1,5-diisocyanate, and mixtures thereof.

### Claim 14 (depends on 12)

The polyurethane elastomer of claim 12 wherein said biobased polyester is selected from the group consisting of poly(1,2-propylene-succinate), poly(1,2-propylene-sebacate), poly(1,3-propylene-succinate), poly(1,3-propylene-sebacate), poly(1,4-butylene-succinate), poly(1,4-butylene-sebacate), poly(1,2-propylene-azeleate), copoly(1,2-propylene succinate)-copoly(1,3-propylene succinate), copoly(1,2-propylene sebacate)-copoly(1,3-propylene sebacate), poly-12-hydroxy stearate, poly-riciniloate, copoly(1,2-propylene succinate)-copoly(12-hydroxy stearate), copoly(1,2-propylene-sebacate)-copoly(12-hydroxy stearate), copoly(1,3-propylene succinate)-copoly(12-hydroxy stearate), copoly(1,3-propylene sebacate)-copoly(12-hydroxy stearate), copoly(1,2-propylene succinate)-copoly(1,2-propylene sebacate), copoly(1,3-propylene succinate)-copoly(1,3-propylene sebacate), terpoly(1,2-propylene succinate)-terpoly(1,3-propylene-succinate)-terpoly(12-hydroxy stearate), copoly(1,2-propylene succinate)-copoly(riciniloate), copoly(1,2-propylene-sebacate)-copoly-(riciniloate), copoly(1,3-propylene succinate)-copoly(riciniloate), copoly(1,3-propylene sebacate)-copoly(12-ricinolate), terpoly(1,2-propylenesuccinate)-terpoly(1,3-propylene-succinate)-terpoly(12-hydroxy stearate), and terpoly(1,2-propylene succinate)-terpoly(1,3-propylene-succinate)-terpoly(riciniloate).

### Claim 15 (depends on 12)

The polyurethane elastomer of claim 12 wherein the hydrolytic stability is from about 80 to about 100 percent for tensile strength, and from about 100 to about 150 percent for elongation.