# US 4,399,270 A · Fiber-forming polyesters of ketodiols

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- Number: US 4,399,270 A
- Document ID: US4399270A
- Status: Granted
- Kind: A
- Application number: 06/402,858
- Filed: 1982-07-29
- Granted: 1983-08-16
- Earliest claimed: 1982-07-29
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: August H. Frazer
- Web page: https://patentgrep.com/patent/US4399270A

## CPC

- C08G 63/19: Hydroxy compounds containing aromatic rings
- C08G 63/6826: {Dicarboxylic acids and dihydroxy compounds}
- D01F 6/62: from polyesters
- D01F 6/84: from copolyesters
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- D01F: CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS

## Abstract

Homopolyesters and copolyesters, of diacids and specific ketodiols, exhibiting melt-anisotropy and being melt-spinnable into oriented filaments that can be heat treated to high tenacity and modulus.

## Claims

### Claim 1

Fiber-forming melt-spinnable polyester that is optically anisotropic in the melt and consists essentially of, respectively:
A. substantially equimolar amounts of the recurring units ##STR12## wherein R.sup.1 is m-phenylene or p-phenylene R.sup.2 is ##STR13## each of R.sup.3, R.sup.4, R.sup.6 and R.sup.7 is independently selected from H, CH.sub.3 and Cl;
R.sup.5 is m-phenylene, p-phenylene, ethylenedioxybis-p-phenylene or p,p'-biphenylene; and
n is 0 or 1; provided, however:
(aa) when n is 0, R.sup.2 is ##STR14## R.sup.3 and R.sup.4 or R.sup.6 and R.sup.7 are both Cl and R.sup.5 is p-phenylene or ethylenedioxybis-p-phenylene, or R.sup.2 is ##STR15## R.sup.3, R.sup.4, R.sup.6 and R.sup.7 and H and R.sup.5 is ethylenedioxybis-p-phenylene; and
(bb) when n is 1, R.sup.1 is m-phenylene, R.sup.2 is ##STR16## R.sup.5 is ethylenedioxybis-p-phenylene or p,p'-biphenylene, one of R.sup.3 and R.sup.4 is CH.sub.3 or Cl and the other is H, and one of R.sup.6 and R.sup.7 is CH.sub.3 or Cl and the other is H; and
B. the recurring units ##STR17## wherein each of X.sup.1 and Y.sup.1 is independently selected from m-phenylene and p-phenylene; ##STR18## each of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 is independently selected from H, CH.sub.3 and Cl;
R.sup.5 is m-phenylene, p-phenylene, ethylenedioxybis-p-phenylene or p,p'-biphenylene; and
n is 0 or 1, each of the recurring units (i) and (ii) comprising 40 to 60 mol % of their combined amounts which is substantially equimolar with the amount of (b), provided, however:
(aa) when n is 0 and one of X.sup.2 and Y.sup.2 is attached at the p-phenylene positions and the other is attached at the m-phenylene positions, then X.sup.3, X.sub.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are H and R.sup.5 is p-phenylene or ethylenedioxybis-p-phenylene;
(bb) when n is 0 and X.sup.2 and Y.sup.2 are both attached at the p-phenylene positions, 1 or 2 of X.sup.3, X.sup.4, X.sup.6 and X.sup.7 and 1 or 2 of Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are independently selected from CH.sub.3 and Cl, the remaining 2 or 3 of X.sup.3, X.sup.4, X.sup.6 and X.sup.7 and the remaining 2 or 3 of Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are H, and R.sup.5 is m-phenylene, p-phenylene or ethylenedioxybis-p-phenylene;
(cc) when n is 0, X.sup.2 and Y.sup.2 are both attached at the p-phenylene positions, and either X.sup.3, X.sup.4, X.sup.6 and X.sup.7 are each independently selected from CH.sub.3 and Cl and Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are H or X.sup.3, X.sup.4, X.sup.6 and X.sup.7 are H and Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are each independently selected from CH.sub.3 and Cl, then R.sup.5 is m-phenylene.
(dd) when n is 0 and X.sup.2 and Y.sup.2 are both attached at the m-phenylene positions, 1 or 2 of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are independently selected from CH.sub.3 and Cl, the remaining 6 or 7 of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are H, and R.sup.5 is is p-phenylene or ethylenedioxybis-p-phenylene;
(ee) when n is 1, X.sup.2 is ##STR19## and Y.sup.2 is ##STR20## (ff) when n is 1 and X.sup.1 and Y.sup.1 are both m-phenylene, 6 of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are independently selected from CH.sub.3 and Cl, the remaining 2 of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are H, and R.sup.5 is p,p'-biphenylene; and
(gg) when n is 1 and one of X.sup.1 and Y.sup.1 is m-phenylene and the other is p-phenylene, each of X.sup.3, X.sup.4, X.sup.6, X.sup.7, Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 is independently selected from CH.sub.3 and Cl, or one of each pair of X.sup.3 and X.sup.4, X.sup.6 and X.sup.7, Y.sup.3 and Y.sup.4 and Y.sup.6 and Y.sup.7 is independently selected from CH.sub.3 and Cl and the other of each pair is H, and R.sup.5 is p,p'-biphenylene.

### Claim 2 (depends on 1)

Hompolyester of claim 1.

### Claim 3 (depends on 2)

Homopolyester of claim 2 wherein
n is 0,
R.sub.2 is ##STR21## R.sup.3 and R.sup.4 are both Cl, R.sup.5 is p-phenylene, and
R.sup.6 and R.sup.7 are both H.

### Claim 4 (depends on 2)

Homopolyester of claim 2 wherein
n is 0,
R.sup.2 is ##STR22## R.sup.3 and R.sup.4 are both Cl, R.sup.5 is ethylenedioxybis-p-phenylene,
R.sup.6 and R.sup.7 are both H.

### Claim 5 (depends on 2)

Homopolyester of claim 2 wherein
n is 0,
R.sup.2 is ##STR23## R.sup.3, R.sup.4, R.sup.6 and R.sup.7 are H, and R.sup.5 is ethylenedioxybis-p-phenylene.

### Claim 6 (depends on 1)

Copolyester of claim 1.

### Claim 7 (depends on 6)

Copolyester of claim 6 wherein
n is 0,
X.sup.2 is ##STR24## X.sup.3, X.sup.4, X.sup.6 and X.sup.7 are H, Y.sup.2 is ##STR25## Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are Cl, and R.sup.5 is m-phenylene.

### Claim 8 (depends on 6)

Copolyester of claim 6 wherein
n is 0,
X.sup.2 is ##STR26## X.sup.3, X.sup.4, X.sup.6 and X.sup.7 are H, Y.sup.2 is ##STR27## Y.sup.3, Y.sup.4, Y.sup.6 and Y.sup.7 are CH.sub.3, and R.sup.5 is m-phenylene.

### Claim 9 (depends on 1)

Shaped article of the polyester of claim 1.

### Claim 10 (depends on 1)

Molded article of the polyester of claim 1.

### Claim 11 (depends on 1)

Extruded article of the polyester of claim 1.

### Claim 12 (depends on 1)

Film of the polyester of claim 1.

### Claim 13 (depends on 1)

Filament of the polyester of claim 1.

### Claim 14 (depends on 3)

Filament of the homopolyester of claim 3.

### Claim 15 (depends on 5)

Filament of the homopolyester of claim 5.

### Claim 16 (depends on 7)

Filament of the copolyester of claim 7.