Method for producing dispersant additives

Patent metadata

Field	Value
Publication number	US-9573103-B2
Application number	US-201214127861-A
Country	US
Kind code	B2
Filing date	May 5, 2012
Priority date	Jun 22, 2011
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

The present invention relates to a method for producing an additive composition which in particular contains specific urea urethanes. The additive composition is extremely suitable as a wetting agent and dispersant.

First claim

The invention claimed is:

1. A method for producing an additive composition, comprising the steps i) to iii), wherein
in step i) a hydroxy component of formula (I)
Y(—OH) q   (I)

 or mixtures thereof,
 wherein
Y is the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical having 1 to 1000 carbon atoms,
q is the same or different and represented by an integer from 1 to 10

is reacted with a diisocyanate of formula (II) having NCO groups of different reactivity
R 1 (NCO) 2   (II)

 or mixtures thereof,
 wherein
R 1 is the same or different and is represented by a hydrocarbon radical having 6 to 20 carbon atoms, comprising an arylene group, a branched or unbranched alkylarylene group, and/or an acyclic, cyclic, branched or unbranched alkylene group,

wherein the diisocyanate of formula (II) is used with respect to the hydroxy component of formula (I) in a molar ratio of at least (1.1*arithmetic mean of q):1.0, so that an isocyanate adduct of formula (III)
Y(—O—CO—NH—R 1 —NCO) q   (III)

 or mixtures thereof,
 wherein
Y, q and R 1 are each as described above,

and unreacted diisocyanate of formula (II) containing reaction mixture is formed,
in step ii) at least 50 mol % of the unreacted portion of the diisocyanate of formula (II) is removed from the reaction mixture,
in step iii) a compound of formula (IV) having at least one head group radical Z 1
Y(—O—CO—NH—R 1 —NH—CO—X—Z 1 ) q   (IV)

 or mixtures thereof,
 wherein
Y, q and R 1 are each as described above,
X is the same or different and is represented by O, NH and/or NZ 2
wherein
Z 2 is 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 a branched or unbranched, saturated or unsaturated organic radical having at least two carbon atoms having at least one head group which is present in salifiable or salified form, and is selected from the group consisting of tertiary amino functions, quaternary ammonium functions, phosphoric acid ester functions, and carboxylic acid functions,

wherein step iii) is carried out in a single stage iii-a) or a sequence of steps iii-b),
in step iii-a) the isocyanate adduct of formula (III) present in the reaction mixture is reacted with an isocyanate-reactive compound of formula (V) having said head group radical Z 1 ,
HX—Z 1   (V)

 wherein
X and Z 1 are each as described above,

and in the sequence of steps iii-b), first, the isocyanate adduct of the formula (III) which is present in the reaction mixture is reacted with a compound having a isocyanate-reactive group HX and at least one further functional group Q, wherein then Q is reacted with a reagent involved in the generation of the head group radical Z 1 to form the head group radical Z 1 .

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

3. A method for the preparation of an additive composition according to claim 1 , characterized in that q=1, so that in the method including steps i) to iii)
in step i) as a hydroxy component a monohydroxy compound of formula (Ia)
Y—OH  (Ia)

 or mixtures thereof,
 wherein
Y is the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical having 1 to 1000 carbon atoms

is reacted with a diisocyanate of formula (II) having NCO groups of different reactivity
R 1 (NCO) 2   (II)

 or mixtures thereof,
 wherein
R 1 is the same or different and is represented by a hydrocarbon radical having 6 to 20 carbon atoms, comprising an arylene group, a branched or unbranched alkylarylene group, and/or an acyclic, cyclic, branched or unbranched alkylene group,

wherein the diisocyanate of formula (II) is used with respect to the monohydroxy component of formula (Ia) in a molar ratio of at least 1.1:1.0, so that a monoisocyanate adduct of formula (IIIa)
Y—O—CO—NH—R 1 —NCO  (IIIa)

 or mixtures thereof,
 wherein
Y and R 1 are each as described above,

and unreacted diisocyanate of formula (II) containing reaction mixture is formed,
in step ii) at least 50 mol % of the unreacted portion of the diisocyanate of formula (II) is removed from the reaction mixture,
in step iii) a compound of formula (IVa) having at least one head group radical Z 1
Y—O—CO—NH—R 1 —NH—CO—X—Z 1   (IVa)

 or mixtures thereof,
 wherein
Y and R 1 are each as described above,
X is the same or different and is represented by O, NH and/or NZ 2
wherein
Z 2 is 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 a branched or unbranched, saturated or unsaturated organic radical having at least two carbon atoms having at least one head group which is present in salifiable or salified form, and is selected from the group consisting of tertiary amino functions, quaternary ammonium functions, phosphoric acid ester functions, and carboxylic acid functions,

wherein step iii) is carried out in a single stage iii-a) or a sequence of steps iii-b),
in step iii-a) the monoisocyanate adduct of formula (IIIa) present in the reaction mixture is reacted with an isocyanate-reactive compound of formula (V) having said head group radical Z 1 ,
HX—Z 1   (V)

 wherein
X and Z 1 are each as described above,

and in the sequence of steps iii-b), first, the monoisocyanate adduct of the formula (IIIa) which is present in the reaction mixture is reacted with a compound having a isocyanate-reactive group HX and at least one further functional group Q, wherein then Q is reacted with a reagent involved in the generation of the head group radical Z 1 to form the head group radical Z 1 .

4. The method according to claim 1 , characterized in that Y contains at least one polyether radical, polyester radical, hydrocarbon radical, and/or polysiloxane radical.

5. The method according to claim 1 , characterized in that Y in total contains 1 to 450 ether oxygen atoms, which optionally are contained in radicals of polytetrahydrofuran, polyoxetanes and/or polyoxiranes.

6. The method according to claim 1 , characterized in that Y in total contains 3 to 400 ether oxygen atoms, wherein at least 50 mol % of the ether oxygen atoms are present in ethylene oxide and/or propylene structural units.

7. The method according to claim 1 , characterized in that R 1 is the same or different and is a tolyl group and/or an isophoronyl group.

8. The method according to claim 1 , characterized in that the diisocyanate of formula (II) is present as toluene-2,4-diisocyanate and/or isophorone diisocyanate.

9. The method according to claim 1 , characterized in that the head group of the head group radical Z 1 is present in the form of a phosphoric acid ester function, step iii) is carried out in the form of a sequence of steps iii-b), wherein the further functional group Q is present in the form of a hydroxyl group and the reagent involved in the generation of the head group moiety Z 1 is present as a phosphorylization agent.

10. The method according to claim 1 , characterized in that the head group radical Z 1 has a phosphoric acid ester function as a head group, wherein Z 1 is the same or different and is represented by formula (VII)
R 2 —O—PO(OR 3 ) n (OH) 2-n   (VII)

wherein
R 2 is the same or different and is represented by a branched or unbranched, saturated or unsaturated organic radical having at least two carbon atoms,
R 3 is the same or different and is represented by a branched or unbra

Assignees

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

Inventors

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

Classifications

• C08G18/61 Primary

  Polysiloxanes · CPC title

• C08G18/0814 Primary

  containing ammonium groups or groups forming them · CPC title

• C09D7/45

  Anti-settling agents · CPC title

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G18/615

  containing carboxylic acid groups · CPC title