Addition compounds suitable as dispersants and dispersion stabilizers

• US 20050250927A1
• Filed: 05/06/2005
• Published: 11/10/2005
• Est. Priority Date: 05/07/2004
• Status: Active Grant

• Current Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Original Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Inventors: Pritschins, Wolfgang, Haubennestel, Karlheinz, Krappe, Udo, Esser, Andrea
• Granted Patent: US 8,362,300 B2
• Time in Patent Office: Days
• US Class Current: 528/44
• CPC Class Codes: C08G 18/2027 having two nitrogen atoms in the ring
• CPC Class Codes: C08G 18/2825 having at least 6 carbon atoms
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/284 Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/6423 Polyalkylene polyamines; polyethylenimines; Derivatives thereof polyamides or polyesteramides C08G18/60
• CPC Class Codes: C08G 18/798 containing urethdione groups
• CPC Class Codes: C09D 17/002 in organic medium C09D17/003, C09D17/004 take precedence
• CPC Class Codes: C09K 23/00 Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
• CPC Class Codes: C09K 23/16 Amines or polyamines
• CPC Class Codes: C09K 23/54 Silicon compounds

Abstract

The present invention provides addition compounds, which suitable as dispersants and as dispersion stabilizers, and to the salts of the said compounds. The invention further provides processes for preparing these addition compounds, to their use as dispersants and dispersion stabilizers for organic and inorganic pigments and also fillers in organic and aqueous systems, and to pulverous or fibrous solids coated with such dispersants and intended for incorporation into liquid systems.

Claims

1. An addition compound prepared by (A) reacting

a) one or more polyisocyanates containing uretdione groups with

b) one or more compounds of the formula (I)

Y—

(XH)_n 

 

(I)

where

XH is a group that can react with isocyanates;

Y is a monomeric or polymeric group that is not reactive towards isocyanates, wherein the Y group comprises at least one aliphatic, cycloaliphatic, araliphatic or aromatic group,

the Y group has a number-average molar mass of less than 20 000 g/mol, and

n is 1, 2 or 3,

wherein at least 50 mol % of the compounds of the formula (I) n is 1;

with the proviso that substantially all free isocyanate groups of component a) are reacted with the compounds of the formula (I) to form an intermediate which contains uretdione groups,

wherein subsequently the uretdione groups are (B) reacted with

c) one or more compounds of the general formula (II)

Z-NHR 

 

(II)

wherein

R is hydrogen or a straight-chain or branched alkyl group having from 1 to 4 carbon atoms; and

Z is an aliphatic, cycloaliphatic or aromatic basic radical; and

,

optionally, after the (B) reaction, reacting any reactive amino groups present in the reaction product with compounds that are reactive towards amino groups; and

salts or quaternization products thereof.

2. The addition compound of claim 1, wherein Y optionally contains the heteroatoms O, S and/or N and/or ether, urethane, carbonate, siloxane and/or ester groups, and optionally halogen is substituted for hydrogen.

3. The addition compound of claim 2, wherein Z has one or more of the following definitions:

A) an aliphatic and/or cycloaliphatic group containing at least one tertiary amino group or

B) a heterocyclic group having at least one basic ring nitrogen atom that contains no hydrogen atom, it being possible for the heterocyclic group to be attached to the group NHR via an organic coupling group, or

C) radical of an optionally modified polyamine and/or polyimine.

4. The addition compound of claim 3, wherein compounds used as Z-NHR are compounds from the group diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, higher linear condensates of the general formula NH₂(C₂H₄NH)_n—

C₂H₄—

NH₂ with n>

5, branched poly(C₂-C₄)alkylenamines, poly(C₂-C₄)alkylenamines, poly(C₂-C₄)alkylenimines having tertiary amino groups and a number-average molecular weight of up to 1 000 000 g/mol or mixtures of such amines.

5. The addition compound of claim 4, wherein in the case of the branched poly(C₂-C₄)alkylenamines of tertiary amino groups the compounds in question are aziridine polymers (polyethylenimines).

6. The addition compound of claim 5, wherein some of the free reactive amino groups present are reacted with epoxides, carbonates, carboxylic acids and/or α

,β

-unsaturated compounds.

7. The addition compound of claim 6, wherein compounds of the formula (I) used are hydroxy-functional polyethers, hydroxy-functional polyesters, hydroxy-functional polyether-polyesters and/or aliphatic and/or cycloaliphatic alcohols having 2 to 30 carbon atoms, some of whose hydrogen atoms may have been replaced by halogen and/or aryl radicals.

8. The addition compound of claim 7, wherein the polyisocyanates containing uretdione groups are cyclic dimerization products of diisocyanates based on hexamethylene diisocyanate, isophorone diisocyanate and/or tolylene diisocyanate.

10. A method for preparing a pigmented paint, wherein the paint comprises a mixture of film-forming binder, solvents, and pigments, optionally including, fillers, and customary paint auxiliaries;

comprising mixing an addition compound of claim 1 with the mixture.

13. A process for preparing an addition compound of claim 1 comprising:

(A) reacting

(a) one or more polyisocyanates containing uretdione groups with

(b) one or more compounds of the formula (I)

Y—

(XH)_n 

 

(I)

where

XH is a group that can react with isocyanates;

Y is a monomeric or polymeric group that is not reactive towards isocyanates, wherein the Y group comprises at least one aliphatic, cycloaliphatic, araliphatic or aromatic groups,

the Y group has a number-average molar mass of less than 20 000 g/mol, and

n is 1, 2 or 3,

wherein at least 50 mol % of the compounds of the formula (1) n is 1;

with the proviso that substantially all free isocyanate groups of component a) are reacted with the compounds of the formula (I) to form an intermediate which contains uretdione groups,

(B) reacting the uretdione groups with

(c) one or more compounds of the general formula (II)

Z-NHR 

 

(II)

wherein

R is hydrogen or a straight-chain or branched alkyl group having from 1 to 4 carbon atoms and

Z is an aliphatic, cycloaliphatic or aromatic basic radical; and

,

(C) optionally reacting any reactive amino groups present in the reaction product with compounds that are reactive towards amino groups, and

(D) optionally reacting the addition compounds with organic or inorganic acids and/or quaternizing agents.

14. A pigment- or filler-composition comprising pigment concentrates, paints, pastes moulding compositions or mixtures thereof;

and an addition compound of claim 1.

15. A method for forming a pigmented coating on a substrate, comprising applying to the substrate, the pigmented paint of claim 10, and baking, curing or crosslinking the coating.

16. A method for forming a dispersible solid powder particle or fibre particle, comprising applying to the particle, an addition compound of claim 1, wherein the addition compound forms a coating on the particles.

9. (canceled)

11. (canceled)

12. (canceled)