IP Library Granted Patent US 9,365,952
Granted Patent B2
US 9,365,952 · App. 13/349,617 · Granted Jun 14, 2016

Copolymer fibers and processes for making same

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Quick Facts
Patent No.
US 9,365,952
App. No.
13/349,617
Granted
Jun 14, 2016
Kind
B2
Abstract

The present invention concerns yarns comprising copolymer derived from the copolymerization of para-phenylenediamine, 5(6)-amino-2-(p-aminophenyl)benzimidazole; and terephthaloyl dichloride wherein the ratio of moles of 5(6)-amino-2-(p-aminophenyl)benzimidazole to the moles of para-phenylenediamine is 30/70 to 85/15. The yarns have a sulfur content greater than 0.1%; and have an effective polymer cation to sulfur content molar ratio of at least 0.3. Additional aspects of the invention concern methods of producing such yarns.

Claims (156)

1. A yarn comprising copolymer derived from the copolymerization of para-phenylenediamine, 5(6)-amino-2-(p-aminophenyl)benzimidazole, and terephthaloyl dichloride wherein the ratio of moles of 5(6)-amino-2-(p-aminophenyl)benzimidazole to the moles of para-phenyienediamine is 30/70 to 85/15, the yarn being spun from a dope comprising the copolymer and sulfuric acid;

said yarn having a sulfur content greater than 0.1%; and

said yarn having an Effective Polymer Cation to Sulfur Content Molar Ratio of at least 0.3 to about 2, wherein said

Effective

Polymer

Cation

to

Sulfur

Content

Molar

Ratio

=

(

[

Na

]

+

2

[

Ca

]

+

[

K

]

-

[

Cl

]

)

[

S

]

where the symbols [Na], [Ca], [K], [Cl], and [S] are the concentration of these ions in moles/kilogram of polymer.

2. The yarn of claim 1 , wherein the ratio of moles of 5(6)-amino-2-(p-aminophenyl)benzimidazole to the moles of para-phenylenediamine is 45/55 to 85/15.

3. The yarn of claim 1 , wherein the Effective Polymer Cation to Sulfur Content Molar Ratio is at least 1.0.

4. The yarn of claim 3 , wherein the Effective Polymer Cation to Sulfur Content Molar Ratio is at least 1.5.

5. A process for treating a yarn derived from the copolymerization of para-phenylenediamine, 5(6)-amino-2-(p-aminophenyl)benzimidazole, and terephthaloyl dichloride, wherein the ratio of moles of 5(6)-amino-2-(p-aminophenyl)benzimidazole to the moles of para-phenylenediamine is 30/70 to 85/15, the yarn being spun from a dope comprising the copolymer and sulfuric acid; said yarn having a sulfur content greater than 0.1%, said process comprising:

washing said yarn with a basic aqueous solution for a time sufficient to provide a yarn having an Effective Polymer Cation to Sulfur Content Molar Ratio of at least 0.3 to about 2; wherein said

Effective

Polymer

Cation

to

Sulfur

Content

Molar

Ratio

=

(

[

Na

]

+

2

[

Ca

]

+

[

K

]

-

[

Cl

]

)

[

S

]

where the symbols [Na], [Ca], [K], [Cl], and [S] are the concentration of these ions in moles/kilogram of polymer.

6. The process of claim 5 , wherein the ratio of moles of 5(6)-amino-2-(p-aminophenyl)benzimidazole to the moles of para-phenylenediamine is 45/55 to 85/15.

7. The process of claim 5 , wherein the Effective Polymer Cation to Sulfur Content Molar Ratio is at least 1.0.

8. The process of claim 7 , wherein the Effective Polymer Cation to Sulfur Content Molar Ratio is at least 1.5.

9. A process for making a yarn from filaments comprising a copolymer derived from the copolymerization of para-phenylenediamine, 5(6)-amino-2-(p-aminophenyl)benzimidazole, and terephthaloyl dichloride having a sulfur content greater than 0.1% comprising the steps of:

a) spinning and collecting a sulfuric acid-laden yarn; and

b) in a separate step, first washing the acid-laden yarn to form a neutralized yarn, followed by heat treating the yarn;

wherein, the neutralizing step provides yarn in which the Effective Polymer Cation to Sulfur Content Molar Ratio is about 0.3 or greater to about 2, wherein said

Effective

Polymer

Cation

to

Sulfur

Content

Molar

Ratio

=

(

[

Na

]

+

2

[

Ca

]

+

[

K

]

-

[

Cl

]

)

[

S

]

where the symbols [Na], [Ca], [K], [Cl], and [S] are the concentration of these ions in moles/kilogram of polymer.

10. The process of claim 9 , wherein the effective polymer cation to sulfur content molar ratio is at least 1.0.

11. The process of claim 10 , wherein the effective polymer cation to sulfur content molar ratio is at least 1.5.

12. The process of claim 9 , further comprising washing said acid-laden yarn with water before and after contacting said yarn with said basic aqueous solution.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT SAFETY & CONSTRUCTION, INC.
Reel/Frame 049585/0450 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2012
From: KNOFF, WARREN FRANCIS; NEWTON, CHRISTOPHER WILLIAM
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 027883/0436 →