# US 9,518,146 B2 · Dispersing additives based on phosphoric acid ester derivatives

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- Number: US 9,518,146 B2
- Document ID: US9518146B2
- Status: Granted
- Kind: B2
- Application number: 14/127,753
- Filed: 2012-05-04
- Published: 2015-02-05
- Granted: 2016-12-13
- Earliest claimed: 2011-06-22
- Assignees: BYK-Chemie GmbH
- Applicants: Bernd Göbelt; Rene Nagelsdiek; Jürgen Omeis; Frederik Piestert; Wolfgang Pritschins; Natasa Meznaric; Daniela Schröder; Werner Tiegs
- Inventors: Bernd Göbelt; Rene Nagelsdiek; Jürgen Omeis; Frederik Piestert; Wolfgang Pritschins; Natasa Meznaric; Daniela Schröder; Werner Tiegs
- Web page: https://patentgrep.com/patent/US9518146B2

## CPC

- C08G 18/836: {by phosphorus containing compounds}
- C08G 18/282: {Alkanols, cycloalkanols or arylalkanols including terpenealcohols}
- C08G 18/2825: {having at least 6 carbon atoms}
- C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds}
- C08G 18/284: {Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids}
- C08G 18/3271: {Hydroxyamines}
- C08G 18/3275: {containing two hydroxy groups}
- C08G 18/4277: {Caprolactone and/or substituted caprolactone}
- C08G 18/4833: {Polyethers containing oxyethylene units}
- C08G 18/61: Polysiloxanes
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 18/833: {by nitrogen containing compounds (by azo compounds C08G18/85)}
- C09D 7/45: Anti-settling agents
- C09K 23/14: Derivatives of phosphoric acid
- C08G 2150/00: Compositions for coatings
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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—R1—NH—CO—X—Z1)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, R1 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 NZ2, Z2 is represented by a branched or unbranched, saturated or unsaturated organic radical, Z1 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.

## Claims

### Claim 1

A phosphoric acid ester derivative according to formula (I)
Y(—O—CO—NH—R1—NH—CO—X—Z1)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,
R1 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 NZ2
wherein
Z2 may be the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical,
Z1 is the same or different and is represented by formula (II)
R2—O—PO(OR3)n(OH)2-n (II)
where
R2 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 R3 is represented by R2—X—CO—NH—R1—NH—CO—O—Y.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

The phosphoric acid ester derivative according to claim 1, characterized in that R1 is a tolyl group.

### Claim 7 (depends on 1)

The phosphoric acid ester derivative according to claim 1, characterized in that R1 is the hydrocarbon radical of a diisocyanate containing two differently reactive NCO groups.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

The phosphoric acid ester derivative according to claim 1, wherein R1 is at least one of an arylene group, a branched or unbranched alkylarylene group, or an acyclic, cyclic, branched or unbranched alkylene group.

### Claim 13 (depends on 4)

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.

### Claim 14 (depends on 7)

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