Polymeric dispersants from phenyl glycidyl ether

Patent metadata

Field	Value
Publication number	US-12398246-B2
Application number	US-202418582837-A
Country	US
Kind code	B2
Filing date	Feb 21, 2024
Priority date	Oct 10, 2017
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

Copolymers comprising recurring units of a phenyl glycidyl ether and alkylene oxides are disclosed. Some of the copolymers comprise a di- or polyfunctional nucleophilic initiator and recurring units of the phenyl glycidyl ether and an alkylene oxide. The di- or polyfunctional nucleophilic initiator is an alcohol, phenol, amine, thiol, thiophenol, sulfinic acid, or deprotonated species thereof. Other copolymers comprise a monofunctional nucleophilic initiator selected from thiols, thiophenols, aralkylated phenols, sulfinic acids, secondary amines, C 10 -C 20 terpene alcohols, and deprotonated species thereof. Pigments dispersions comprising the copolymers are also disclosed. The copolymers meet the growing needs of the industry with their ease of manufacture, diverse structures, and desirable performance attributes for dispersing a wide range of organic and inorganic pigments. Agricultural applications for the copolymers are also disclosed.

First claim

We claim:

1. A dispersion comprising a pigment, water, a pH adjusting agent, and a copolymer comprising a reaction product of:
(a) a polyhydroxyl nucleophilic initiator selected from the group consisting of alcohols, phenols, and deprotonated species thereof, the initiator containing from 2 to 6 nucleophilic moieties;
(b) from 1 to 30 recurring units per active hydrogen equivalent of the initiator of a phenyl glycidyl ether; and
(c) from 1 to 100 recurring units per active hydrogen equivalent of the initiator of one or more alkylene oxides (AO) selected from the group consisting of ethylene oxide, propylene oxide, butylene oxides, and combinations thereof;
wherein the copolymer comprises 20 to 60 wt. % of the phenyl glycidyl ether recurring units based on the combined amounts of the phenyl glycidyl ether and AO recurring units, and the copolymer comprises branches wherein a branch is defined as a segment of the copolymer composed of a block of phenyl glycidyl ether followed by a block of AO units, the number of branches being an integer and uniformly equal to the number of nucleophilic moieties; and

wherein the copolymer has a number-average molecular weight within the range of 1,900 to 56,000 g/mol.

2. The dispersion of claim 1 wherein the pigment is an organic pigment selected from the group consisting of monoazos, diazos, anthraquinones, anthrapyrimidines, quinacridones, quinophthalones, dioxazines, flavanthrones, indanthrones, isoindolines, isoindolinones, metal complexes, perinones, perylenes, phthalocyanines, pyranthrones, thioindigos, triphenylmethanes, anilines, benzimidazolones, diarylides, diketopyrrolopyrroles, naphthols, and aldazines.

3. The dispersion of claim 1 wherein the pigment is an inorganic pigment selected from the group consisting of white pigments, black pigments, chromatic pigments, and luster pigments.

4. A wettable polymer composition comprising 80 to 95 wt. % of at least one agricultural active, 0.1 to 5 wt. % of an anionic surfactant, and 1 to 20 wt. % of a copolymer comprising a reaction product of:
(a) a polyhydroxyl nucleophilic initiator selected from the group consisting of alcohols, phenols, and deprotonated species thereof, the initiator containing from 2 to 6 nucleophilic moieties;
(b) from 1 to 30 recurring units per active hydrogen equivalent of the initiator of a phenyl glycidyl ether; and
(c) from 1 to 100 recurring units per active hydrogen equivalent of the initiator of one or more alkylene oxides (AO) selected from the group consisting of ethylene oxide, propylene oxide, butylene oxides, and combinations thereof;
wherein the copolymer comprises 20 to 60 wt. % of the phenyl glycidyl ether recurring units based on the combined amounts of the phenyl glycidyl ether and AO recurring units, and the copolymer comprises branches wherein a branch is defined as a segment of the copolymer composed of a block of phenyl glycidyl ether followed by a block of AO units, the number of branches being an integer and uniformly equal to the number of nucleophilic moieties; and

wherein the copolymer has a number-average molecular weight within the range of 1,900 to 56,000 g/mol.

5. A suspension concentrate comprising 20 to 60 wt. % of at least one agricultural active, 25 to 75 wt. % of water, and 0.5 to 3.5 wt. % of a copolymer comprising a reaction product of:
(a) a polyhydroxyl nucleophilic initiator selected from the group consisting of alcohols, phenols, and deprotonated species thereof, the initiator containing from 2 to 6 nucleophilic moieties;
(b) from 1 to 30 recurring units per active hydrogen equivalent of the initiator of a phenyl glycidyl ether; and
(c) from 1 to 100 recurring units per active hydrogen equivalent of the initiator of one or more alkylene oxides (AO) selected from the group consisting of ethylene oxide, propylene oxide, butylene oxides, and combinations thereof;
wherein the copolymer comprises 20 to 60 wt. % of the phenyl glycidyl ether recurring units based on the combined amounts of the phenyl glycidyl ether and AO recurring units, and the copolymer comprises branches wherein a branch is defined as a segment of the copolymer composed of a block of phenyl glycidyl ether followed by a block of AO units, the number of branches being an integer and uniformly equal to the number of nucleophilic moieties; and
wherein the copolymer has a number-average molecular weight within the range of 1,900 to 56,000 g/mol.

6. A water-dispersible granule or a seed coating comprising an agricultural active and a copolymer comprising a reaction product of:
(a) a polyhydroxyl nucleophilic initiator selected from the group consisting of alcohols, phenols, and deprotonated species thereof, the initiator containing from 2 to 6 nucleophilic moieties;
(b) from 1 to 30 recurring units per active hydrogen equivalent of the initiator of a phenyl glycidyl ether; and
(c) from 1 to 100 recurring units per active hydrogen equivalent of the initiator of one or more alkylene oxides (AO) selected from the group consisting of ethylene oxide, propylene oxide, butylene oxides, and combinations thereof;
wherein the copolymer comprises 20 to 60 wt. % of the phenyl glycidyl ether recurring units based on the combined amounts of the phenyl glycidyl ether and AO recurring units, and the copolymer comprises branches wherein a branch is defined as a segment of the copolymer composed of a block of phenyl glycidyl ether followed by a block of AO units, the number of branches being an integer and uniformly equal to the number of nucleophilic moieties; and
wherein the copolymer has a number-average molecular weight within the range of 1,900 to 56,000 g/mol.

Assignees

• Stepan Co

Inventors

• Boebel Timothy A
• Dong Xue Min
• Rojas E Carolina
• Luka Renee
• Luebke Gary
• Knox Paul W

Classifications

• C09D5/027

  Dispersing agents (anti-settling agents C09D7/45) · CPC title

• C09D5/022

  Emulsions, e.g. oil in water · CPC title

• C08L2201/54

  Aqueous solutions or dispersions · CPC title

• C08L71/02

  Polyalkylene oxides · CPC title

• C08J2421/02

  Latex · CPC title