Ionic diol, antistatic polyurethane, and method of making the same

Patent metadata

Field	Value
Publication number	US-10308753-B2
Application number	US-201515532881-A
Country	US
Kind code	B2
Filing date	Dec 8, 2015
Priority date	Dec 16, 2014
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

An ionic diol has formula wherein R 1 represents an alkyl group having from 6 to 18 carbon atoms; R 2 and R 3 independently represent alkyl groups having from 1 to 4 carbon atoms; R 4 represents an alkylene group having from 2 to 8 carbon atoms; and R 5 represents an alkylene group having from 1 to 8 carbon atoms. Antistatic polymers are formed by copolymerization of monomers including a diisocyanate, an ionic diol, a polyether diol, and at least one non-ionic diols. Methods of making the antistatic polyurethanes are also disclosed.

First claim

What is claimed is:

1. An ionic diol represented by the formula:

wherein
R 1 represents an alkyl group having from 6 to 18 carbon atoms;
R 2 and R 3 independently represent alkyl groups having from 1 to 4 carbon atoms;
R 4 represents an alkylene group having from 2 to 8 carbon atoms; and
R 5 represents an alkylene group having from 1 to 8 carbon atoms.

2. The ionic diol of claim 1 , wherein R 1 has from 6 to 10 carbon atoms.

3. The ionic diol of claim 1 , wherein R 2 and R 3 are independently methyl or ethyl.

4. The ionic diol of claim 1 , wherein R 4 has from 2 to 4 carbon atoms.

5. The ionic diol of claim 1 , wherein R 5 has from 2 to 4 carbon atoms.

6. An antistatic polyurethane having a polymer backbone comprising:
at least one divalent segment a) represented by formula

wherein
R 1 represents an alkyl group having from 6 to 18 carbon atoms,
R 2 and R 3 independently represent alkyl groups having from 1 to 4 carbon atoms,
R 4 represents an alkylene group having from 2 to 18 carbon atoms, and
R 5 represents an alkylene group having from 2 to 18 carbon atoms;

divalent segments b) represented by the formula

 wherein
R 6 represents a divalent organic group having from 2 to 18 carbon atoms, wherein at least one of the divalent segments b) is adjacent to at least one of the divalent segments a);

divalent segments c) represented by the formula

 wherein
R 7 represents a divalent organic group having from 2 to 12 carbon atoms, and
w represents a positive integer, wherein at least one of the divalent segments c) is adjacent to at least one of the divalent segments b); and

divalent segments d) represented by the formula

 wherein
 each R 8 independently represents an alkylene group having from 1 to 8 carbon atoms,
 each R 9 independently represents an alkyl group having from 1 to 4 carbon atoms,
 each R 10 independently represents H or an alkyl group having from 1 to 8 carbon atoms, and

v represents a positive integer, wherein at least one of the divalent segments d) is adjacent to at least one of the divalent segments b), wherein terminal carbonyl groups on adjacent divalent segments are not directly bonded to each other, and wherein terminal —O— groups on adjacent divalent segments are not directly bonded to each other.

7. The antistatic polyurethane of claim 6 , wherein R 1 has from 6 to 10 carbon atoms.

8. The antistatic polyurethane of claim 6 , wherein R 2 and R 3 are independently methyl or ethyl.

9. The antistatic polyurethane of claim 6 , wherein R 4 has from 2 to 4 carbon atoms.

10. The antistatic polyurethane of claim 6 , wherein R 5 has from 2 to 4 carbon atoms.

11. The antistatic polyurethane of claim 6 , wherein R 6 has from 12 to 16 carbon atoms.

12. The antistatic polyurethane of claim 6 , wherein R7 is ethylene or propylene.

13. The antistatic polyurethane of claim 6 , wherein R 8 has from 1 to 4 carbon atoms.

14. A method of making an antistatic polyurethane, the method comprising steps:
a) reacting a first diol with a molar excess of a diisocyanate to form a first prepolymer, wherein the first diol is represented by formula

 wherein
R 1 represents an alkyl group having from 6 to 18 carbon atoms;
R 2 and R 3 independently represent alkyl groups having from 1 to 4 carbon atoms;
R 4 represents an alkylene group having from 2 to 18 carbon atoms
R 5 represents an alkylene group having from 2 to 18 carbon atoms; and

wherein the diisocyanate is represented by the formula
OCN—R 6 —NCO

wherein R 6 represents a divalent organic group having from 2 to 18 carbon atoms;

b) reacting the first prepolymer with a second diol to form a second prepolymer, wherein the second diol is represented by the formula

wherein
R 7 represents a divalent organic group having from 2 to 12 carbon atoms,
w represents a positive integer; and

c) reacting the second prepolymer with a third diol to form the antistatic polyurethane,
wherein the third diol is represented by the formula

wherein
each R 8 independently represents an alkylene group having from 1 to 8 carbon atoms,
each R 9 independently represents an alkyl group having from 1 to 4 carbon atoms,
each R 10 independently represents H or an alkyl group having from 1 to 8 carbon atoms, and
v represents a positive integer.

15. The method of claim 14 , wherein R 1 has from 6 to 10 carbon atoms.

16. The method of claim 14 , wherein R 2 and R 3 are independently methyl or ethyl.

17. The method of claim 14 , wherein R 4 has from 2 to 4 carbon atoms.

18. The method of claim 14 , wherein R 5 has from 2 to 4 carbon atoms.

19. The method of claim 14 , wherein R 6 has from 12 to 16 carbon atoms.

20. The method of claim 14 , wherein R 7 is ethylene or propylene.

21. The method of claim 14 , wherein R 8 has from 1 to 4 carbon atoms.

22. The method of claim 14 , wherein step c) provides a third prepolymer, the method further comprising d) reacting the third prepolymer with at least one of an alkanediol or an alkanediamine having from 2 to 8 carbon atoms.

23. An antistatic polyurethane made according to the method of claim 14 .

Assignees

• 3M Innovative Properties Co

Inventors

• Yang Yu
• Kehren Jason M
• Lu Yongshang
• Iyer Suresh S
• Lamanna William M
• Klun Thomas P
• Peterson Jeffrey A

Classifications

• C08G18/44

  Polycarbonates · CPC title

• C08G18/3819

  having nitrogen · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• C07C311/48

  having nitrogen atoms of sulfonamide groups further bound to another hetero atom · CPC title