# US 2019/0169399 A1 · Plastic modifiers

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- Number: US 2019/0169399 A1
- Document ID: US20190169399A1
- Status: Published application
- Kind: A1
- Application number: 16/270,158
- Filed: 2019-02-07
- Published: 2019-06-06
- Earliest claimed: 2015-05-07
- Assignees: Novus International, Inc.
- Applicants: Novus International Inc.
- Inventors: Graciela B. Arhancet; Xiaojun Wang; Scott Long; Matthew William Mahoney
- Web page: https://patentgrep.com/patent/US20190169399A1

## CPC

- C08K 5/372: Sulfides {, e.g. R-(S)x-R'}
- C07C 319/20: by reactions not involving the formation of sulfide groups
- C07C 323/52: the carbon skeleton being acyclic and saturated
- C08G 63/6882: {derived from hydroxy carboxylic acids}
- C08G 63/912: {derived from hydroxycarboxylic acids}
- C08K 5/41: Compounds containing sulfur bound to oxygen
- C08L 67/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Hydrocarbyl terminated polyester compounds comprising sulfur-containing repeat units that are useful as plastic modifiers, polymer blend compositions comprising the hydrocarbyl terminated polyester compounds, methods for modifying the performance properties of polymers, and methods for preparing the hydrocarbyl terminated polyester compounds.

## Claims

### Claim 1

A process for preparing a distribution of compounds of Formula (Ia) from a compound of Formula (III), the process comprising:
(a) contacting the compound of Formula (III) with an alcohol, R3OH, to form a distribution of compounds of Formula (II); and
(b) contacting the distribution of compounds of Formula (II) with an acyl halide or its acid analog, R4C(O)X, to form the distribution of compounds of Formula (Ia);
wherein:
R1, R3, and R4 independently are hydrocarbyl or substituted hydrocarbyl;
X is a halide ion or a hydroxyl group;
Z is sulfur, sulfoxide, or sulfone;
k is an integer of 1 or greater; and
n is an integer of 1 or greater.

### Claim 2 (depends on 1)

The process of claim 1, wherein R1 is alkyl; and R3 and R4 independently are alkyl, substituted alky, alkenyl, or substituted alkenyl.

### Claim 3 (depends on 1)

The process of claim 1, wherein R1 is C1 to C6 alkyl; and R3 and R4 independently are C1 to C30 alkyl or C1 to C30 alkenyl.

### Claim 4 (depends on 3)

The process of claim 3, wherein R1 is methyl; Z is sulfur; k is from 1 to 20; and n is 2.

### Claim 5 (depends on 1)

The process of claim 1, wherein the compound of Formula (III) and the alcohol, R3OH, are present at a mole-to-mole ratio of about 1:0.1 to about 1:10;

### Claim 6 (depends on 1)

The process of claim 1, wherein step (a) is conducted in the presence of a catalyst and at a temperature of about 80° C. to about 150° C.

### Claim 7 (depends on 1)

The process of claim 1, wherein the distribution of compounds of Formula (II) and R4C(O)X are present at a mole-to-mole ratio of about 1:0.8 to about 1:1.5.

### Claim 8 (depends on 1)

The process of claim 1, wherein step (b) is conducted at a temperature of about 70° C. to about 90° C.

### Claim 9 (depends on 1)

The process of claim 1, further comprising contacting the distribution of compounds of Formula (Ia) with one or more agents to remove color bodies and/or odor.

### Claim 10

A process for preparing a distribution of compounds of Formula (Ia) from a compound of Formula (IV), the process comprising:
(a) contacting the compound of Formula (IV) with an alcohol, R3OH, to form a distribution of compounds of Formula (II); and
(b) contacting the distribution of compounds of Formula (II) with an acyl halide or its acid analog, R4C(O)X, to form the distribution of compounds of Formula (Ia);
wherein:
R1, R3, and R4 independently are hydrocarbyl or substituted hydrocarbyl;
X is a halide ion or a hydroxyl group;
Z is sulfur, sulfoxide, or sulfone;
k is an integer of 1 or greater; and
n is an integer of 1 or greater.

### Claim 11 (depends on 10)

The process of claim 10, wherein R1 is alkyl; and R3 and R4 independently are alkyl, substituted alky, alkenyl, or substituted alkenyl.

### Claim 12 (depends on 10)

The process of claim 10, wherein R1 is C1 to C6 alkyl; and R3 and R4 independently are C1 to C30 alkyl or C1 to C30 alkenyl.

### Claim 13 (depends on 12)

The process of claim 12, wherein R1 is methyl; Z is sulfur; k is from 1 to 20; and n is 2.

### Claim 14 (depends on 10)

The process of claim 10, wherein the compound of Formula (III) and the alcohol, R3OH, are present at a mole-to-mole ratio of about 1:0.1 to about 1:10.

### Claim 15 (depends on 10)

The process of claim 10, wherein step (a) is conducted in the presence of a catalyst and at a temperature of about 80° C. to about 150° C.

### Claim 16 (depends on 10)

The process of claim 10, wherein the compound of Formula (II) and R4C(O)X are present at a mole-to-mole ratio of about 1:0.8 to about 1:1.5.

### Claim 17 (depends on 10)

The process of claim 10, wherein step (b) is conducted at a temperature of about 70° C. to about 90° C.

### Claim 18 (depends on 10)

The process of claim 10, further comprising contacting the distribution of compounds of Formula (Ia) with one or more agents to remove color bodies and/or odor.