# US 8,772,420 B2 · Fluorinated polyester blend

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- Number: US 8,772,420 B2
- Document ID: US8772420B2
- Status: Granted
- Kind: B2
- Application number: 13/338,310
- Filed: 2011-12-28
- Published: 2013-01-03
- Granted: 2014-07-08
- Earliest claimed: 2010-12-28
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: Neville Everton Drysdale; Fredrik Nederberg
- Inventors: Neville Everton Drysdale; Fredrik Nederberg
- Web page: https://patentgrep.com/patent/US8772420B2

## CPC

- C08G 63/6826: {Dicarboxylic acids and dihydroxy compounds}
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08L 2205/02: containing two or more polymers of the same C08L -group
- 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

A fluorinated polyester blend is prepared by melt blending a fluorovinyl ether functionalized polyester with a non-fluorinated polyester. The fluoroether functionalized polyester can be a homopolymer or a copolymer. The blend is useful for preparing fibers, yarns, fabrics, garments, carpets, and other shaped articles. The shaped articles exhibit durable soil, oil, and water repellency.

## Claims

### Claim 1

A blend composition comprising a first aromatic polyester selected from the group consisting of poly(trimethylene terephthalate) (PTT), poly(ethylene naphthalate) (PEN), poly(ethylene isophthalate), poly(trimethylene isophthalate), poly(butylene isophthalate), mixtures thereof, and copolymers thereof, and a second aromatic polyester in contact therewith, wherein the second aromatic polyester is present in the composition at a concentration in the range of 0.1 to 10% by weight of the total composition; and, wherein the second aromatic polyester comprises a molar concentration in the range of 40 to 100 mol-% of fluorovinylether functionalized repeat units represented by structure I
wherein,
Ar represents a benzene or naphthalene radical;
each R is independently H, C1-C10 alkyl, C5-C15 aryl, C6-C20 arylalkyl; OH, or a radical represented by structure II
with the proviso that only one R can be OH or the radical represented by the structure (II) II;
R1 is a C2-C4 alkylene radical which can be branched or unbranched;
X is O or CF2;
Z is H or Cl;
a=0 or 1;
and,
Q represents structure Ia
wherein q=0-10;
Y is O or CF2;
Rf1 is (CF2)n, wherein n is 0-10;
and,
Rf2 is (CF2)p, wherein p is 0-10, with the proviso that when p is 0, Y is CF2.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the first aromatic polyester is poly(trimethylene terephthalate).

### Claim 3 (depends on 1)

The composition of claim 1 wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure I is dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate.

### Claim 4 (depends on 3)

The composition of claim 3 wherein the dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy) isophthalate is present at a molar concentration in the range of 40 to 60 mol-%.

### Claim 5 (depends on 1)

The composition of claim 1 wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure I is dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate.

### Claim 6 (depends on 5)

The composition of claim 5 wherein the dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy) isophthalate is present at a molar concentration in the range of 40 to 60 mol-%.

### Claim 7 (depends on 1)

The composition of claim 1 wherein the first aromatic polyester is poly(trimethylene terephthalate), the second aromatic polyester is present at a concentration in the range of 1-3% by weight, wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure I is dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate present at a molar concentration of 40-60 mol-%.

### Claim 8

A process of producing a blend composition comprising combining a first aromatic polyester selected from the group consisting of poly(trimethylene terephthalate) (PTT), poly(ethylene naphthalate) (PEN), poly(ethylene isophthalate), poly(trimethylene isophthalate), poly(butylene isophthalate), mixtures thereof, and copolymers thereof, with a second aromatic polyester to form a combination wherein the second aromatic polyester is present in the combination at a concentration in the range of 0.1 to 10% by weight of the total composition; heating the combination to a temperature between the softening point of the first aromatic polyester and the degradation temperature of at least one component of the combination to form a viscous liquid mixture, and mixing the viscous liquid mixture; the second aromatic polyester comprising a molar concentration in the range of 40 to 100 mol-% of fluorovinylether functionalized repeat units represented by structure I
wherein,
Ar represents a benzene or naphthalene radical;
each R is independently H, C1-C10 alkyl, C5-C15 aryl, C6-C20 arylalkyl; OH, or a radical represented by structure II
with the proviso that only one R can be OH or the radical represented by the structure II;
R1 is a C2-C4 alkylene radical which can be branched or unbranched;
X is O or CF2;
Z is H or Cl;
a=0 or 1;
and,
Q represents the structure Ia
wherein q=0-10;
Y is O or CF2;
Rf1 is (CF2)n, wherein n is 0-10;
and,
Rf2 is (CF2)p, wherein p is 0-10, with the proviso that when p is 0, Y is CF2.

### Claim 9 (depends on 8)

The process of claim 8 wherein the first aromatic polyester is poly(trimethylene terephthalate).

### Claim 10 (depends on 8)

The process of claim 8 wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure I is dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate.

### Claim 11 (depends on 10)

The process of claim 10 wherein the dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate is present at a molar concentration in the range of 40 to 60 mol-%.

### Claim 12 (depends on 8)

The process of claim 8 wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure I is dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate.

### Claim 13 (depends on 12)

The process of claim 12 wherein the dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate is present at a molar concentration in the range of 40 to 60 mol-%.

### Claim 14 (depends on 8)

The process of claim 8 wherein the first aromatic polyester is poly(trimethylene terephthalate), the second aromatic polyester is present at a concentration in the range of 1-3% by weight, wherein the second aromatic polyester the fluorovinylether functionalized repeat unit represented by the structure t is dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate present at a molar concentration of 40-60 mol-%.