Wetting agents and dispersants having rheological character

Patent metadata

Field	Value
Publication number	US-10752801-B2
Application number	US-201816231666-A
Country	US
Kind code	B2
Filing date	Dec 24, 2018
Priority date	Dec 27, 2017
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

A polyaddition compound and/or a salt thereof is obtainable by the reaction of epoxy resin based on at least one diglycidyl ether of Formula (I)

wherein R=a divalent aliphatic or monocyclic aromatic or bicyclic aromatic radical or mixtures thereof; with at least one polyether alcohol of Formula (II)

R 1 -[OEt] n -[OPr] m -[OBu] s -[OSO] r -OH  Formula (II)

wherein R 1 =independently identical or different, linear or branched, optionally aromatic hydrocarbyl radicals having 1 to 18 carbon atoms, [OEt]=ethylene oxide radical, [OPr]=propylene oxide radical, [OBu]=butylene oxide radical, [OSO]=styrene oxide radical, n=0 to 100, m=0 to 50, s=0 to 20, and r=0 to 3, with the proviso that n+m+s+r=3-103, and with at least one compound containing at least one functional group selected from sulfate groups, sulfonate groups, carboxylate groups and phosphate groups.

First claim

The invention claimed is:

1. A polyaddition compound and/or a salt thereof, obtainable by the reaction of an epoxy resin based on at least one diglycidyl ether of Formula (I)

wherein R=a divalent aliphatic or monocyclic aromatic or bicyclic aromatic radical or mixtures thereof,
with at least one polyether alcohol of Formula (II)
R 1 -[OEt] n -[OPr] m -[OBu] s -[OSO] r -OH  Formula (II)

wherein
R1=independently identical or different, linear or branched, optionally aromatic hydrocarbyl radicals having 1 to 18 carbon atoms,
[OEt]=ethylene oxide radical,
[OPr]=propylene oxide radical,
[OBu]=butylene oxide radical,
[OSO]=styrene oxide radical,
n=0 to 100,
m=0 to 50,
s=0 to 20, and
r=0 to 3,
with the proviso that n+m+s+r=3-103,
and
with at least one compound containing at least one functional group selected from the group consisting of sulfate groups, sulfonate groups, carboxylate groups and phosphate groups.

2. The polyaddition compound according to claim 1 , wherein the diglycidyl ether of the Formula (I) is selected from diglycidyl ethers of difunctional saturated or unsaturated, branched or unbranched, cyclic or open-chain C2-C30 alcohols, diglycidyl ethers of difunctional polyether polyols of low to high molecular weight, or from diglycidyl ethers of difunctional unsubstituted or substituted, monocyclic, polycyclic and/or fused diphenols or triphenols selected from 1,4-dihydroxybenzene, 1,3-dihydroxybenzene, 1,2-dihydroxybenzene, 1,3-dihydroxytoiuene, 3,5-dihydroxybenzoate, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(4-hydroxyphenyi)methane (bisphenol F), bis(4-hydroxyphenyl) sulfone (bisphenol S), naphthoresorcinol, dihydroxynaphthalene, dihydroxyanthraquinone, dihydroxybiphenyl, 3,3-bis(p-hydroxyphenyl)phthalide, 5,5-bis(4-bydroxyphenyl)hexahydro-4,7-methanoindane, phenolphthalein, fluorescein, 4,4′-[bis(hydroxyphenyl)-1,3-phenylenebis(1-methylethylidene)] (bisphenol M), 4,4′-[bis(hydroxyphenyl)-1,4-phenylenebis(1-methylethylidene)] (bisphenol P), or 2,2′-diallyl bisphenol A.

3. The polyaddition compound according to claim 1 , wherein the reaction is conducted in the presence of a reaction catalyst.

4. The polyaddition compound according to claim 3 , wherein the reaction catalyst is selected from sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, strontium hydroxide, alkali metal alkoxides, the alkali metal salts of carboxylic acids, inorganic protic acids, organic protic acids, Lewis acids and complexes thereof, aliphatic, cycloaliphatic, araliphatic amines, nitrogen heterocycles, tertiary amines, quaternary ammonium salts or mixtures thereof.

5. The polyaddition compound according to claim 1 , wherein the compound containing a functional group is selected from sulfuric acid, chlorosulfonic acid and sulfur trioxide for formation of sulfate groups, polyphosphoric acid, phosphoric acid, phosphorus pentoxide and phosphorus pentachloride for formation of phosphate groups, acid anhydride and chloroacetic acid for formation of carboxylate groups, propane sulfone, butane sultone and 3-chloro-2-hydroxypropanesulfonic acid for formation of sulfonate groups, and/or salts thereof.

6. A process for preparing a polyaddition compound and/or a salt thereof, the process comprising:
reacting an epoxy resin based on at least one diglycidyl ether of Formula (I)

wherein R=a divalent aliphatic or monocyclic aromatic or bicyclic aromatic radical or mixtures thereof
with at least one polyether alcohol of Formula (II)
R 1 -[OEt] n -[OPr] m -[OBu] s -[OSO] r -OH  Formula (II)

wherein
R 1 =independently identical or different, linear or branched, optionally aromatic hydrocarbyl radicals having 1 to 18 carbon atoms,
[OEt]=ethylene oxide radical,
[OPr]=propylene oxide radical,
[OBu]=butylene oxide radical,
[OSO]=styrene oxide radical, n=0 to 100, m=0 to 50, s=0 to 20, and r=0 to 3,
with the proviso that n+m+s+r=3-103, at a temperature between 25° C. and 300° C.,
then reacting with at least one compound containing at least one functional group selected from the group consisting of sulfate groups, sulfonate groups, carboxylate groups and phosphate groups.

7. The process according to claim 6 , wherein the molar ratio of the epoxy groups of diglycidyl ether of Formula (I) to the OH groups of the polyether alcohol of Formula (II) is 10:0.5 to 10:4.0.

8. The process according to claim 6 , wherein the compound containing a functional group is selected from sulfuric acid, chlorosulfonic acid and sulfur trioxide for formation of sulfate groups, polyphosphoric acid, phosphoric acid, phosphorus pentoxide and phosphorus pentachloride for formation of phosphate groups, acid anhydride and chloroacetic acid for formation of carboxylate groups, propane sultone, butane sultone and 3-chloro-2-hydroxypropanesulfonic acid for formation of sulfonate groups, and/or salts thereof.

9. The process according to claim 8 , wherein the hydroxyl groups in the polyether alcohols of Formula (II) are partially or fully converted to phosphate groups, sulfate groups, sulfonate groups or carboxylate groups.

10. The process according to claim 6 , wherein the reaction is conducted in the presence of a reaction catalyst.

11. The process according to claim 6 , wherein the reaction catalyst is at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, strontium hydroxide, alkali metal alkoxides, alkali metal salts of carboxylic acids, inorganic and organic protic acids, Lewis acids and complexes thereof, aliphatic, cycloaliphatic, araliphatic amines, nitrogen heterocycles, tertiary amines, and quaternary ammonium salts.

12. The process according to claim 6 , wherein the diglycidyl ether of the Formula (I) is selected from the group consisting of diglycidyl ethers of difunctional saturated or unsaturated, branched or unbranched, cyclic or open-chain C2-C30 alcohols, selected from ethylene glycol, butanediol, hexanediol, octanediol glycidyl ethers, cyclohexanedimethanol diglycidyl ethers and neopentyl glycol diglycidyl ethers, from diglycidyl ethers of difunctional polyether polyols of low to high molecular weight, selected from polyethylene glycol diglycidyl ethers or polypropylene glycol diglycidyl ethers, or from diglycidyl ethers of difunctional unsubstituted or substituted, monocyclic, polycyclic and/or fused diphenols or triphenols selected from 1,4-dihydroxybenzene, 1,3-dibydroxybenzene, 1,2-dihydroxybenzene, 1,3-dihydroxytoiuene, 3,5-dihydroxybenzoate, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(4-hydroxyphenyl)methane (bisphenol F), bis(4-hydroxyphenyl) sulfone (bisphenol S), naphthoresorcinol, dihydroxynaphthalene, dihydroxyanthraquinone, dihydroxybiphenyl, 3,3-bis(p-hydroxyphenyl)phthalide, 5,5-bis(4-hydroxyphenyl)hexahydro-4,7-methanoindane, phenolphthalein, fluorescein, 4,4′-[bis(hydroxyphenyl)-1,3-phenylenebis(1-methylethylidene)] (bisphenol M), 4,4′-[bis(hydroxyphenyl)-1,4-phenylenebis(1-methylethylidene)] (bisphenol P), and 2,2′-diailyl bisphenol A.

13. A composition, comprising: at least one particulate solid, and
a polyaddition compound and/or salt thereof according to claim 1 .

14. The composition according to claim 13 , which, when in the form

Assignees

• Evonik Operations Gmbh

Inventors

• Favresse Philippe
• Grewing Manuela
• Kleinsteinberg Frank
• Roediger Sandra
• Flock Birgit

Classifications

• C08G59/1488

  containing phosphorus · CPC title

• C08G59/1483

  containing sulfur · CPC title

• C08G59/1444 Primary

  Monoalcohols · CPC title

• C09D11/037

  characterised by the pigment · CPC title

• C09D7/65

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title