Softening thermoplastic polyurethanes using ionomer technology

Patent metadata

Field	Value
Publication number	US-10227440-B2
Application number	US-201615166948-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 27, 2015
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

In one or more embodiments, the present invention provides a novel approach to the addition of plasticizers for softening TPUs, i.e., lowering the durometer and the melt viscosity. This approach involves incorporating bonded sulfonate groups with quaternary ammonium counterions into the TPU. In one or more embodiments of the present invention, the softening of TPU is achieved by incorporating an ionic diol, such as N,N-bis (2-hydoxyethyl)-2-aminoethane-sulfonic acid (BES), coupled with various bulky alkyl ammonium cations, during the chain extension step of the TPU synthesis. It is believed that that steric hindrance of the bulky quaternary ammonium groups weakens the dipole-dipole interactions of the sulfonate groups and/or lowers the crystallinity of the hard block, thereby creating additional free volume that softens the polymer and lowers the melt viscosity.

First claim

What is claimed is:

1. A chain extender for use in softening non water-soluble thermoplastic polyurethanes comprising a sulfonic acid containing polyol anion and a quaternary ammonium cation and having a formula selected from:

wherein l is an integer from 1 to 20; m is an integer from 1 to 20; and n is an integer from 1 to 18, and the nitrogen atom of the quaternary ammonium cation contains no more than three methyl side groups.

2. The chain extender of claim 1 having the formula:

wherein n is an integer from 5 to 18.

3. The chain extender of claim 1 having the formula:

wherein l is an integer from 1 to 20; m is an integer from 1 to 20; and n is an integer from 5 to 18.

4. A chain extender comprising a sulfonic acid containing polyol anion and a quaternary ammonium cation and having the formula:

wherein each n is an integer from 1 to 18 and the nitrogen atom of the quaternary ammonium cation contains no more than three methyl side groups.

5. The chain extender of claim 1 wherein said quaternary ammonium cation has the formula:

6. The chain extender of claim 4 wherein said quaternary ammonium cation has the formula:

7. The chain extender of claim 1 wherein said quaternary ammonium cation has the formula:

8. The chain extender of claim 4 wherein said quaternary ammonium cation has the formula:

9. The chain extender of claim 4 wherein said quaternary ammonium cation has the formula:

10. The chain extender of claim 1 wherein said quaternary ammonium cation has the formula:

11. The chain extender of claim 4 wherein said quaternary ammonium cation has the formula:

Assignees

• Becker Matthew
• Weiss Robert A
• Zander Zachary Kurtiss
• Wardius Don S
• Haider Karl W
• Lawrey Bruce D
• Univ Akron
• Covestro Llc

Inventors

• Becker Matthew
• Weiss Robert A
• Zander Zachary Kurtiss
• Wardius Don S
• Haider Karl W
• Lawrey Bruce D

Classifications

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/42

  Polycondensates having carboxylic or carbonic ester groups in the main chain · CPC title

• C08G18/0828

  containing sulfonate groups or groups forming them · CPC title

• C08G18/48

  Polyethers · CPC title