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US 12,043,705 B2Granted
Pigment dispersant for coating
AssigneeBASF Coatings GmbH
InventorsShampa R. Samanta, Chintankumar Patel, Qingling Zhang, Karel Hartlieb, Benjamin Georg Robert Mohr
Life of this patent
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Abstract
Described herein is a polymeric pigment dispersant, a process for preparation of the polymeric pigment dispersant and a pigment dispersion including the pigment dispersant that is used for coating and in printing ink, automotive basecoat, auto-motive clearcoat, mill base, furniture coatings and wood coatings.
Claims13
A polymeric pigment dispersant comprising a polymer backbone and at least one moiety of the formula (I):
- wherein
- R1 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- R2 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- R3 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- R4 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- R5 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- R6 is selected from the group consisting of H, —OH, a —C(═O)—O— group, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—O— group and at least one phenyl which is substituted with at least one —OH;
- or
- R5 and R6 together with the carbon atoms to which they are bonded form an unsubstituted phenyl or substituted phenyl which is substituted with at least one —OH;
- whereby the at least one phenyl in each case is optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, I, —NO2, —CN, —C1-C6l -alkyl, —CHF2, —CH2F, —CF3, cyclopropyl, —O—C1-C6-alkyl, —C(═O)—C1-C6-alkyl, —C(═O)—O—C1-C6-alkyl, —C(═O)—O—phenyl and —CH2—C(═O)—C1-C6-alkyl;
- whereby at least two of R1, R2, R3, R4, R5 and R6 are —OH or comprise —OH and one of R1, R2, R3, R4, R5 and R6 is a —C(═O)—O— group or comprises a —C(═O)—O— group;
- and
- whereby the moiety of formula (I) is bonded to the polymer backbone via a —C(═O)—O— group;
- wherein,
- the polymer backbone is a linear di-block polymer or a random polymer,
- wherein,
- the random polymer is obtainable by reacting a mixture (M) comprising:
- (a) glycidyl (meth)acrylate and/or glycidyl acrylate;
- and
- (b) at least one monomer selected from the group consisting of alkyl (meth)acrylate, hydroxyalkyl (meth)acrylate and cycloalkyl (meth)acrylate.
17 more elements
A process for the preparation of at least one polymeric pigment dispersant comprising at least the steps of:
- reacting a di-block polymer with a compound of the formula (II):
- wherein
- R1 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one -OH;
- R2 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R3 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R4 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R5 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R6 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- or
- R5 and R6 together with the carbon atoms to which they are bonded form an unsubstituted phenyl or substituted phenyl which is substituted with at least one —OH;
- whereby the at least one phenyl in each case are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, I, —NO2, —CN, —C1-C6-alkyl, —CHF2, —CH2F, —CF3, cyclopropyl, —O—C1-C6-alkyl, —C(═O)—C1-C6-alkyl, —C(═O)—O—C1-C6-alkyl, —C(═O)—O—phenyl and —CH2—C(═O)—C1-C6-alkyl;
- whereby at least two of R1, R2, R3, R4, R5 and R6 are —OH or comprise —OH and one of R1, R2, R3, R4, R5 and R6 is a —C(═O)—OH or comprises a —C(═O)—OH;
- at a temperature from ≥80° C. to ≤150° C.;
- and
- wherein the linear di-block copolymer comprises a first and a second block and is obtained by a living free radical polymerization, optionally in the presence of a solvent.
12 more elements
A process for the preparation of at least one polymeric pigment dispersant comprising at least the steps of:
- (a) reacting a random polymer with a compound of the formula (II):
- wherein
- R1 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R2 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R3 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R4 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R5 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R6 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- or
- R5 and R6 together with the carbon atoms to which they are bonded form an unsubstituted phenyl or substituted phenyl which is substituted with at least one —OH;
- whereby the at least one phenyl in each case are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, I, —NO2, —CN, —C1-C6-alkyl, —CHF2, —CH2F, —CF3, cyclopropyl, —O—C1-C6-alkyl, —C(═O)—C1-C6-alkyl, —C(═O)—O—C1-C6-alkyl, —C(═O)—O—phenyl and —CH2—C(═O)—C1-C6-alkyl;
- whereby at least two of R1, R2, R3, R4, R5 and R6 are —OH or comprise —OH and one of R1, R2, R3, R4, R5 and R6 is a —C(═O)—OH or comprises a —C(═O)—OH;
- and
- (b) reacting the compound obtained in step (a) with at least one monomer of a lactone at a temperature from ≥30° C. to ≤190° C.
11 more elements
A process for the preparation of at least one polymeric pigment dispersant comprising at least the steps of:
- (a) reacting at least one polyalkylene glycol monoalkyl ether and at least one carboxylic acid anhydride at a temperature in the range from ≥70° C. to ≤140° C. to obtain a mixture;
- and
- (b) reacting the mixture obtained in step (a) with a random polymer and a compound of the formula (II):
- wherein
- R1 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R2 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R3 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R4 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R5 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- R6 is selected from the group consisting of H, —OH, a —C(═O)—OH, a linear or a branched, substituted C1-C14 alkyl and a linear or branched, substituted C2-C14 alkenyl, whereby the alkyl and the alkenyl are each substituted with one —C(═O)—OH and at least one phenyl which is substituted with at least one —OH;
- or
- R5 and R6 together with the carbon atoms to which they are bonded form an unsubstituted phenyl or substituted phenyl which is substituted with at least one —OH;
- whereby at least two of R1, R2, R3, R4, R5 and R6 are —OH or comprise —OH and one of R1, R2, R3, R4, R5 and R6 is a —C(═O)—OH or comprises a —C(═O)—OH;
- whereby the at least one phenyl in each case are optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of F, Cl, Br, I, —NO2, —CN, —C1-C6-alkyl, —CHF2, —CH2F, —CF3, cyclopropyl, —O—C1-C6-alkyl, —C(═O)—C1-C6-alkyl, —C(═O)—O—C1-C6-alkyl, —C(═O)—O—phenyl and —CH2—C(═O)—C1-C6-alkyl;
- at a temperature in the range from ≥70° C. to ≤140° C.
12 more elements
Dependencies are inferred from the claim text.