Polyether-modified epoxy amine adducts as wetting and dispersing agents

Patent metadata

Field	Value
Publication number	US-9340641-B2
Application number	US-201013511587-A
Country	US
Kind code	B2
Filing date	Dec 8, 2010
Priority date	Dec 11, 2009
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

Addition compound suitable as wetting and dispersing agent, obtainable from the reaction of
A) polyepoxides with B) at least one primary polyoxyalkyleneamine C) at least one other aliphatic and/or araliphatic primary amine and D) at least one modified isocyanate.

First claim

The invention claimed is:

1. An addition compound suitable as wetting and dispersing agent, obtained by:
the reaction of:
A) polyepoxides,
B) at least one primary polyoxyalkyleneamine of the general formula (I)

where R is selected from the group consisting of C 1 -C 24 alkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, and C 6 -C 18 aralkyl, R 1 and R 2 are each independently selected from the group consisting of H, C 1 -C 24 alkyl, aryl, and alkoxymethyl, and x is at least 2 yielding a blockwise or random arrangement, and
C) at least one other aliphatic and/or araliphatic primary amine of the general formula (II)
H 2 N—R 6 —Z  (II)

where R 6 is selected from the group consisting of alkyl, cycloalkyl, aryl and aralkyl, Z is an optional substituent group selected from the group consisting of —OH, tertiary amine, and a heterocyclic radical with a 5- or 6-membered ring, to form epoxide-terminated polymers comprising reactive hydroxyl groups or amine-terminated polymers comprising reactive hydroxyl groups; and
reacting the epoxide-terminated polymers comprising reactive hydroxyl groups or amine-terminated polymers comprising reactive hydroxyl groups with:

D) at least one modified isocyanate of the general formula (IIIa) and/or (IIIb)

where R 3 is selected from the group consisting of alkyl, cycloalkyl, aryl, and aralkyl, R 4 and R 5 are each independently selected from the group consisting of H, alkyl, and aryl, X is selected from the group consisting of alkylene, cycloalkylene, and aralkylene, Y is selected from the group consisting of alkylene and cycloalkylene, and n and m are independently 0 to 100, where the sum n+m≧2,
to form a urethane.

2. The addition compound as claimed in claim 1 , wherein component A are diepoxides of the general formula (IV)

with S is —CH 2 —O— or —CH 2 —, T is selected from the group consisting of alkylene, cycloalkylene, arylene, and aralkylene, and u is 1-8.

3. The addition compound as claimed in claim 1 , wherein the component B are polyethylene glycol-polypropylene glycols having a terminal primary amino group, which are prepared starting from methanol and are based on ethylene oxide and propylene oxide.

4. The addition compound as claimed in claim 1 , wherein in a further step any terminal amino groups present are reacted with isocyanates, lactones, cyclic carbonates or (meth)acrylates.

5. The addition compound as claimed in claim 1 , wherein in a further step any terminal epoxide groups present are reacted with secondary amines or saturated or unsaturated carboxylic acids.

6. The addition compound as claimed in claim 1 , wherein in a further step any remaining hydroxyl functions are reacted with hydroxycarboxylic acids and/or cyclic lactones.

7. The addition compound as claimed in claim 1 , wherein in a further step any remaining hydroxyl functions are reacted with unsaturated cyclic anhydrides with retention of the double bond for radiation curing.

8. The addition compound as claimed in claim 1 , wherein in a further step any remaining hydroxyl functions are reacted with (meth)acrylic acid and/or (meth)acrylic esters with retention of the double bond for radiation curing.

9. The addition compound as claimed in claim 1 , wherein in a further step any remaining hydroxyl functions are reacted with isocyanates other than those set out under D.

10. The addition compound as claimed in claim 1 , wherein in a further step any remaining hydroxyl functions are reacted with phosphoric acid or polyphosphoric acid and/or acidic phosphoric esters and/or carboxylic acids.

11. The addition compound as claimed in claim 1 , wherein in a further step there is an alkylation or oxidation of any remaining amino groups to form quaternary ammonium salts or nitrogen oxides.

12. The addition compound as claimed in claim 1 , wherein x is from 10 to 100.

13. The addition compound as claimed in claim 1 , wherein x is from 20 to 70.

14. The addition compound as claimed in claim 1 , wherein x is from 35 to 50.

15. The addition compound as claimed in claim 1 , wherein the alkoxymethyl is CH 3 OCH 2 .

16. The addition compound as in claimed in claim 15 , wherein x is from 10 to 100.

17. The addition compound as claimed in claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of C 1 -C 24 alkyl, and aryl.

18. The addition compound as in claimed in claim 17 , wherein x is from 10 to 100.

19. A wetting and/or dispersing agent for organic and/or inorganic pigments or fillers comprising the addition compound as claimed in claim 1 .

20. Solids in powder or fiber form that are coated with the addition compounds as claimed in claim 1 .

21. A process for preparing an addition compound suitable as wetting and dispersing agent, comprising:
reacting:
A) polyepoxides,
B) at least one primary polyoxyalkyleneamine of the general formula (I)

where R is selected from the group consisting of C 1 -C 24 alkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, and C 6 -C 18 aralkyl, R 1 and R 2 are each independently selected from the group consisting of H, C 1 -C 24 alkyl, aryl, and alkoxymethyl, and x is at least 2 yielding a blockwise or random arrangement, and
C) at least one other aliphatic and/or araliphatic primary amine of the general formula (II)
H 2 N—R 6 —Z  (II)

where R 6 is selected from the group consisting of alkyl, cycloalkyl, aryl and aralkyl, Z is an optional substituent group selected from the group consisting of —OH, tertiary amine, and a heterocyclic radical with a 5- or 6-membered ring, to form epoxide-terminated polymers comprising reactive hydroxyl groups or amine-terminated polymers comprising reactive hydroxyl groups; and
reacting the epoxide-terminated polymers comprising reactive hydroxyl groups or amine-terminated polymers comprising reactive hydroxyl groups with:

D) at least one modified isocyanate of the general formula (IIIa) and/or (IIIb)

where R 3 is selected from the group consisting of alkyl, cycloalkyl, aryl, and aralkyl, R 4 and R 5 are each independently selected from the group consisting of H, alkyl, and aryl, X is selected from the group consisting of alkylene, cycloalkylene, and aralkylene, Y is selected from the group consisting of alkylene and cycloalkylene, and n and m are independently 0 to 100, where the sum n+m≧2,
to form a urethane.

22. The process as claimed in claim 21 , wherein component A are diepoxides of the general formula (IV)

with S is —CH 2 —O— or —CH 2 —, T is selected from the group consisting of alkylene, cycloalkylene, arylene, and aralkylene, and u is 1-8.

Assignees

• Orth Ulrich
• Holtkamp Heribert
• Omeis Jürgen
• Byk Chemie Gmbh

Inventors

• Orth Ulrich
• Holtkamp Heribert
• Omeis Jürgen

Classifications

• C08G59/184 Primary

  with amines · CPC title

• C08G18/8064

  with monohydroxy compounds · CPC title

• C08G18/643

  Reaction products of epoxy resins with at least equivalent amounts of amines · CPC title

• C08G59/4028

  Isocyanates; Thioisocyanates · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title