Dispersing additives based on phosphoric acid ester derivatives

Patent metadata

Field	Value
Publication number	US-9518146-B2
Application number	US-201214127753-A
Country	US
Kind code	B2
Filing date	May 4, 2012
Priority date	Jun 22, 2011
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

Phosphoric acid derivatives, which are present as urea urethanes and contain a radical with an affinity for the binder in addition to at least one phosphoric acid ester group. Said phosphoric acid derivatives are especially suitable as wetting agents and dispersants. The derivatives are present according to the general formula (I)

Y(—O—CO—NH—R 1 —NH—CO—X—Z 1 ) g   (I)
wherein Y is represented by a branched or unbranched, saturated or unsaturated organic radical containing 1 to 1000 carbon atoms, q is represented by an integer from 1 to 10, R 1 is represented by a saturated or unsaturated, branched or unbranched organic radical containing 6 to 20 carbon atoms, X is represented by NH and/or NZ 2 , Z 2 is represented by a branched or unbranched, saturated or unsaturated organic radical, Z 1 is represented by a branched or unbranched, saturated or unsaturated organic radical, which contains at least two carbon atoms and at least one phosphoric acid ester group.

First claim

The invention claimed is:

1. A phosphoric acid ester derivative according to formula (I)
Y(—O—CO—NH—R 1 —NH—CO—X—Z 1 ) g   (I)

or mixtures thereof,
where
Y is the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical containing 1 to 1000 carbon atoms,
q may be the same or different and is represented by an integer from 1 to 10,
R 1 may be the same or different and is represented by a hydrocarbon radical containing 6 to 20 carbon atoms,
X may be the same or different and is represented by NH and/or NZ 2
wherein
Z 2 may be the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical,
Z 1 is the same or different and is represented by formula (II)
R 2 —O—PO(OR 3 ) n (OH) 2-n   (II)

where
R 2 is the same or different and is represented by a saturated or unsaturated, branched or unbranched organic radical containing at least two carbon atoms,

characterized in that n is 1 and R 3 is represented by R 2 —X—CO—NH—R 1 —NH—CO—O—Y.

2. The phosphoric acid ester derivative according to claim 1 , characterized in that q is the same or different and is represented by an integer from 1 to 5.

3. The phosphoric acid ester derivative according to claim 1 , characterized in that Y contains at least one polyether radical, polyester radical, hydrocarbon radical and/or polysiloxane radical.

4. The phosphoric acid ester derivative according to claim 1 , characterized in that Y contains a total of 1 to 450 ether oxygen atoms.

5. The phosphoric acid ester derivative according to claim 1 , characterized in that Y contains a total of 3 to 400 ether oxygen atoms, at least 50 mol % of the ether oxygen atoms being present in ethylene oxide and/or propylene oxide structural units.

6. The phosphoric acid ester derivative according to claim 1 , characterized in that R 1 is a tolyl group.

7. The phosphoric acid ester derivative according to claim 1 , characterized in that R 1 is the hydrocarbon radical of a diisocyanate containing two differently reactive NCO groups.

8. The phosphoric acid ester derivative according to claim 1 , which is present in salinized or partially salinized form.

9. A process comprising adding the phosphoric acid ester derivative according to claim 1 to coatings, varnish coatings, plastics, pigment pastes, sealing compounds, ceramics, cosmetics, adhesives, casting compounds, spackling compounds, inks and printing inks.

10. A solid mixture containing particles and/or fibers that have been treated with the phosphoric acid ester derivative according to claim 1 .

11. A coating and/or plastic containing the phosphoric acid ester derivative according to claim 1 .

12. The phosphoric acid ester derivative according to claim 1 , wherein R 1 is at least one of an arylene group, a branched or unbranched alkylarylene group, or an acyclic, cyclic, branched or unbranched alkylene group.

13. The phosphoric acid ester derivative according to claim 4 , wherein the ether oxygen atoms of Y are contained in radicals of at least one of polytetrahydrofuran, polyoxetanes or polyoxiranes.

14. The phosphoric acid ester derivative according to claim 7 , wherein the diisocyanate is at least one of toluene 2,4-diisocyanate or isophorone diisocyanate.

Assignees

• Göbelt Bernd
• Nagelsdiek Rene
• Omeis Jürgen
• Piestert Frederik
• Pritschins Wolfgang
• Meznaric Natasa
• Schröder Daniela
• Tiegs Werner
• Byk Chemie Gmbh

Inventors

• Göbelt Bernd
• Nagelsdiek Rene
• Omeis Jürgen
• Piestert Frederik
• Pritschins Wolfgang
• Meznaric Natasa
• Schröder Daniela
• Tiegs Werner

Classifications

• C08G2150/00

  Compositions for coatings · CPC title

• C08G18/4277

  Caprolactone and/or substituted caprolactone · CPC title

• C08G18/836 Primary

  by phosphorus containing compounds · CPC title

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title