Ionic diol, antistatic polyurethane, and method of making the same
Assignee3M Innovative Properties Company
InventorsYu Yang, Jason M. Kehren, Yongshang Lu, Suresh S. Iyer, William M. Lamanna, Thomas P. Klun, Jeffrey A. Peterson
Life of this patent
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Abstract
An ionic diol has formula wherein R1 represents an alkyl group having from 6 to 18 carbon atoms; R2 and R3 independently represent alkyl groups having from 1 to 4 carbon atoms; R4 represents an alkylene group having from 2 to 8 carbon atoms; and R5 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.
Claims23
An ionic diol represented by the formula:
- wherein
- R1 represents an alkyl group having from 6 to 18 carbon atoms;
- R2 and R3 independently represent alkyl groups having from 1 to 4 carbon atoms;
- R4 represents an alkylene group having from 2 to 8 carbon atoms;
- and
- R5 represents an alkylene group having from 1 to 8 carbon atoms.
An antistatic polyurethane having a polymer backbone comprising:
- at least one divalent segment a) represented by formula
- wherein
- R1 represents an alkyl group having from 6 to 18 carbon atoms,
- R2 and R3 independently represent alkyl groups having from 1 to 4 carbon atoms,
- R4 represents an alkylene group having from 2 to 18 carbon atoms, and
- R5 represents an alkylene group having from 2 to 18 carbon atoms;
- divalent segments b) represented by the formula
- wherein
- R6 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
- R7 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 R8 independently represents an alkylene group having from 1 to 8 carbon atoms,
- each R9 independently represents an alkyl group having from 1 to 4 carbon atoms,
- each R10 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.
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
- R1 represents an alkyl group having from 6 to 18 carbon atoms;
- R2 and R3 independently represent alkyl groups having from 1 to 4 carbon atoms;
- R4 represents an alkylene group having from 2 to 18 carbon atoms
- R5 represents an alkylene group having from 2 to 18 carbon atoms;
- and
- wherein the diisocyanate is represented by the formula
- OCN—R6—NCO
- wherein R6 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
- R7 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 R8 independently represents an alkylene group having from 1 to 8 carbon atoms,
- each R9 independently represents an alkyl group having from 1 to 4 carbon atoms,
- each R10 independently represents H or an alkyl group having from 1 to 8 carbon atoms, and
- v represents a positive integer.
Dependencies are inferred from the claim text.